Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative
A fused-ring aromatic hydrocarbon and disubstituted technology, which is applied in the field of preparation of 1,8-disubstituted naphthalene-based condensed-ring aromatic hydrocarbon mononitration derivatives, can solve problems such as poor selectivity, poor substrate universality, and many wastes, and achieve low cost Low, high product yield and high purity effect
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Embodiment 1
[0026]
[0027] 3.12g (20mmol, M=156.23) 1,8-dimethylnaphthalene (I-1), 9.29g (23 mmol, M=404.00) Fe(NO 3 ) 3 9H 2 O was added to 26mL CH 3 In COOH, the temperature was controlled at 40°C for 5 hours, and the end point of the reaction was monitored by TLC until the disappearance of the raw material point. Cool to room temperature, filter with suction, and use a small amount of H 2 O and anhydrous C 2 h 5 The filter cake was washed with OH and vacuum-dried to obtain the light yellow product 4-nitro-1,8-dimethylnaphthalene (II-1) with a yield of 92%. HPLC purity 98.6%. HRMS(ES+)C 12 h 12 NO 2 ([M+H]) + The theoretical value is 202.0868, and the measured value is 202.0866.
Embodiment 2
[0029]
[0030] 3.20g (20mmol, M=160.17) 1,8-dihydroxynaphthalene (I-2), 5.35g (23 mmol, M=232.59) Cu(NO 3 ) 2 2.5H 2 O was added to 13mL CH 3 COOH+13 mL(CH 3 CO) 2 In O, the temperature was controlled at 25°C for 5 h. Other conditions and preparation steps were the same as in Example 1 to obtain the orange-yellow product 4-nitro-1,8-naphthalenediol (II-2) with a yield of 91%. HPLC purity 99.2%. HRMS(ES+)C 10 h 8 NO 4 ([M+H]) + The theoretical value is 206.0453, and the measured value is 206.0453.
Embodiment 3
[0032]
[0033] 3.16g (20mmol, M=158.20) 1,8-diaminonaphthalene (I-3), 9.29g (23 mmol, M=404.00) Fe(NO 3 ) 3 9H 2 O was added to 13mL CH 3 COOH+13mL (CH 3 CO) 2 In O, the temperature was controlled at 25°C for 5 h. Other conditions and preparation steps were the same as in Example 1 to obtain the orange-red product 4-nitro-1,8-naphthalenediamine (II-3) with a yield of 94%. HPLC purity 99.0%. HRMS(ES+)C 10 h 10 N 3 o 2([M+H]) + The theoretical value is 204.0773, and the measured value is 204.0774.
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