Hydrochloric Acid → 5-Nitro-2-(3-phenylpropylamino)benzoic acid

HRID 982036Notes

Reaction equation

HRID 982036 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:14]1([CH2:20][CH2:21][CH2:22][NH2:23])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.Cl>CC(N(C)C)=O>[N+:11]([C:8]1[CH:9]=[CH:10][C:2]([NH:23][CH2:22][CH2:21][CH2:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 162593-PhenylpropylamineHCID 172872-Chloro-5-nitrobenzoic acid

Product 1

HCID 45495-Nitro-2-(3-phenylpropylamino)benzoic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A solution of 15.3 g of 2-chloro-5-nitrobenzoic acid and 49 g of 3-phenylpropylamine in 60 ml of dimethylacetamide is heated at 145° C. for 2 hours. After cooling, 300 ml of water are added, and the mixture is acidified (pH 2 to 1) with 2 N HCl.

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-b4dbf659a3694623bb7dda461ecb6be5
Source dataset
uspto-grants-1991_02
Patent number
US04994493

Reaction notes

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