Ethanol → Ethyl 3-benzylamino-5-nitro-4-phenylbenzoate

HRID 1605543Notes

Reaction equation

HRID 1605543 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=[O:6].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH2:28](O)[CH3:29]>>[CH2:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:17]([O-:19])=[O:18])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH2:28][CH3:29])=[O:6])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 7498Benzyl Bromide2×HCID 124087693-Amino-5-nitro-4-phenylbenzoic acid

Product 1

HCID 21546889Ethyl 3-benzylamino-5-nitro-4-phenylbenzoate

Procedure

A mixture of 3-amino-5-nitro-4-phenylbenzoic acid (4.0 g), benzylbromide (4.0 ml), and ethanol (40 ml) is refluxed for 40 hours. After 16 and 24 hours additional amounts of benzylbromide (each portion 2.0 ml) are added. After cooling, the mixture is evaporated in vacuo and the obtained crude ethyl 3-benzylamino-5-nitro-4-phenylbenzoate is saponified by heating with a mixture of 2 N sodium hydroxide (25 ml) and ethanol (25 ml) for about 1 hour. The cooled mixture is acidified with acetic acid (5 ml) and diluted with water (15 ml). After cooling at about 5° C for 48 hours, the resulting precipitate is collected by filtration, washed with water and dried. After recrystallization from aqueous ethanol, 3-benzylamino-5-nitro-4-phenylbenzoic acid is obtained with a melting point of 188°-189° C.

Workup

  1. temperatureis refluxed for 40 hours
  2. temperatureAfter cooling
  3. customthe mixture is evaporated in vacuo

Sources & evidence

ORD record
ord-bea3b2f74ac64d7e9780887f3e1ef765
Source dataset
uspto-grants-1976_04
Patent number
US03950380

Reaction notes

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