Preparation method of naftifine hydrochloride
A technology of naftifine hydrochloride and naftifine, which is applied in the preparation of carboxylic acid amides, organic compounds, amino compounds, etc., can solve the problems of difficult product structure diversification, complex process, and numerous steps, and achieve improved Productivity, simple operation process, and the effect of reducing production costs
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Embodiment 1
[0022] (1) N-Methyl-1-naphthamide 2 Synthesis: Reference preparation ( Eur. J. Org. Chem. 2003, 2132-2137): N 2 Atmosphere and stirring at room temperature, the SOCl 2 (4.00 mL, 548.0 mmol) add 1-naphthoic acid dropwise 1 (45.6 mmol), the resulting mixture was heated to 80°C and reacted for 2 h; after the reaction, the unreacted SOCl was removed under reduced pressure 2 The residue was dissolved in dichloromethane (4 mL); methylamine aqueous solution (46.8 mmol) was added, the reaction was stirred at room temperature for 12 h, and then the reaction solution was poured into saturated NaHCO 3 (500 mL) in the solution, extract with dichloromethane (3×150 mL), combine the organic phases, and MgSO 4 After drying and concentrating, N-methyl-1-naphthamide 2 was obtained with a yield of 92%, mp 159-160°C. 1 H NMR: CDCl 3 , 400 MHz. δ (ppm): 8.20 (m, 1 H), 7.81 (m, 2 H), 7.82-7.31 (m, 4 H), 6.37 (br, 1 H), 2.93 (s, 3 H) ; 13 C NMR: CDCl 3 , 100 MHz. δ (ppm): 170.2, 134.3, 133.4, 130.2,...
Embodiment 2
[0027] (1) N-Methyl-1-naphthamide 2 Synthesis: the same as in Example 1.
[0028] (2) N-methyl-N-allyl substituted-1-naphthamide 3 Synthesis of: FeCl catalyst 3 (20% mmol), the solvent xylene was changed to THF (50 mL), the reaction temperature was 140° C., and the reaction time was 5 hours. Others were the same as in Example 1. N-methyl-N-allyl substituted-1-naphthamide 3 The yield was 83%.
[0029] (3) Naftifine 4 Synthesis of the reaction: the reaction was heated at 80°C for 5h; the unreacted hydrazine hydrate was distilled off, the temperature was raised to 180-210°C, and the reaction was continued for 1 h. Others were the same as in Example 1.
[0030] (4) Naftifine hydrochloride 5 Synthesis: the same as in Example 1. The total yield of naftifine hydrochloride was 60.8%.
Embodiment 3
[0032] (1) N-Methyl-1-naphthamide 2 Synthesis: the same as in Example 1.
[0033] (2) N-methyl-N-allyl substituted-1-naphthamide 3 Synthesis: The catalyst is BF 3 ·OEt 2 (20% mmol), the solvent xylene was changed to dioxane (50 mL), the reaction temperature was 50° C., and the reaction time was 24 hours. Others were the same as in Example 1. N-methyl-N-allyl substituted-1-naphthamide 3 The yield was 85.5%.
[0034] (3) Naftifine 4 Synthesis of: KOH: 20 mmol), 85% hydrazine hydrate added dropwise 2.0 mL (65 mmol), react at 95 ℃ and heat for 3 hours; distill out unreacted hydrazine hydrate, heat up to 190~200 ℃, continue the reaction for 3 h , Others are the same as in Example 1.
[0035] (4) Synthesis of Naftifine Hydrochloride 5: Same as Example 1. The total yield of naftifine hydrochloride was 62.5%.
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