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Preparation method and key intermediate of antineoplastic reagent 4-iodo-3-nitrobenzamide

A technology of nitrobenzamide and intermediates, applied in the field of preparation of 4-iodo-3-nitrobenzamide, can solve the problems of low yield, poor reaction selectivity, low purity, etc., and achieve increased yield and The effect of purity

Inactive Publication Date: 2013-09-04
江苏万全特创医药生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main disadvantage is that the selectivity of the reaction is poor, the yield is low, and the purity is low

Method used

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  • Preparation method and key intermediate of antineoplastic reagent 4-iodo-3-nitrobenzamide
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  • Preparation method and key intermediate of antineoplastic reagent 4-iodo-3-nitrobenzamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of 4-cyano-2-nitroaniline (compound II).

[0030]

[0031] In a 500ml three-necked flask, add 21.6g (0.1mol) of compound I, 10g (0.12mol) of cuprous cyanide, and 200ml of DMF, stir, heat up to 60°C and react for 5h, TLC detection shows that the reaction is complete, and cool to room temperature , distilled, and the solvent was removed to obtain a residue, which was extracted with ethyl acetate (20ml×3), distilled under reduced pressure, and recrystallized from ethanol to obtain 14.5g of a reddish solid, yield: 70.2%.

[0032] MS (+1): 164.

[0033] 1H NMR: d (ppm, CDCl3), 8.19 (s, 1H), 7.64-7.65 (d, 1H), 6.92-6.93 (d, 1H), 4.237-4.24 (br, 2H).

Embodiment 2

[0034] Embodiment 2: Preparation of 4-iodo-3-nitrobenzonitrile (compound III)

[0035]

[0036] Add 32.6g of Intermediate II (0.2mol), 540mL of distilled water, and 50mL of concentrated hydrochloric acid into a 2L three-neck flask, stir mechanically, cool down to 0-5°C in an ice bath, and the reaction solution is a yellow slurry. Dissolve 20.7g of sodium nitrite (0.3mol) in 230mL of water, and slowly add it dropwise to the above reaction system, some solids will dissolve, control the temperature in the system at 0-5°C, continue stirring to complete the addition, and control the temperature to react for 3h. Filtrate with suction to obtain a yellow solid and filtrate, and transfer the filtrate to a 3L three-neck flask. Dissolve 66g of potassium iodide (0.4mol) in 148mL of water, slowly add it dropwise into the reaction system, a large amount of air bubbles are generated, after the addition, continue to stir for 2h, and filter with suction to obtain an orange-red filter cake, ...

Embodiment 3

[0039] Embodiment 3: the preparation of 4-iodo-3-nitrobenzamide (compound TM)

[0040]

[0041] In a 250ml three-neck flask, add 27.5g (0.1mmol) of compound III and 200ml of concentrated hydrochloric acid, stir, heat up to 80°C for 5 hours, TLC spotting test shows that the reaction is complete, cool to room temperature, precipitate solid, suction filter, vacuum dry , to obtain 26.3 g of white solid, yield: 90.1%.

[0042] MS (+1): 293.

[0043] HNMR: d (ppm, CDCl3), 8.65 (s, 1H), 8.11-8.12 (d, 1H), 8.08-8.09 (d, 1H), 6.12-6.13 (s, 2H).

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Abstract

The invention belongs to the field of medicinal chemistry, relates to a preparation method of 4-iodo-3-nitrobenzamide. The preparation method comprises the following steps: in an organic solvent, carrying out a nitrile grouping reaction on a compound I and cuprous cyanide to obtain an intermediate II; carrying out a diazotization-iodo-elimination reaction on the obtained intermediate II to obtain an intermediate III; and hydrolyzing the intermediate III to obtain a target compound 4-iodo-3-nitrobenzamide.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method of 4-iodo-3-nitrobenzamide and a key intermediate thereof. Background technique [0002] 4-iodo-3-nitrobenzamide, a polyadenosine diphosphate-ribose polymerase inhibitor, is currently in clinical research as an antitumor agent. Has good clinical prospects. [0003] Its main preparation method is as follows at present: [0004] [0005] The main disadvantage is that the selectivity of the reaction is poor, the yield is low, and the purity is low. Contents of the invention [0006] The object of the present invention is to provide a new preparation method of 4-iodo-3-nitrobenzamide, which can obviously improve the yield and quality of 4-iodo-3-nitrobenzoyl. [0007] Specific steps are as follows: [0008] (1) In an organic solvent, a nitrile reaction occurs between compound I and cuprous cyanide to obtain intermediate II; [0009] (2) The intermediate ...

Claims

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Application Information

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IPC IPC(8): C07C205/58C07C201/12C07C255/49C07C253/30
Inventor 翟富民郭夏宋雪梅
Owner 江苏万全特创医药生物技术有限公司
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