Phenylacetic Acid → HCID 178526479, compound

HRID 566378Notes

Reaction equation

HRID 566378 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-:3])=[O:2].[C:12]1([CH2:18][C:19](O)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>Cl>[CH2:18]([C:19]1[NH:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[N:11]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 999Phenylacetic AcidHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 178526479HCID 178526479, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A misture of 4-nitro-o-phenylene diamine (1.54 g) and phenylacetic acid (2.04 g) in 5N aqueous HCl (16 ml) were heated at 110° C. under nitrogen for 22 hours. The mixture was cooled to room temperature and the accumulated black solid collected by filtration. This crude residue was then adsorbed onto silica and chromatographed to give the title compound (0.84 g) as a purple foam; δH CDCl3 9.70 (1H, bs), 8.15 (1H, d), 7.30 (7H, m), 4.30 (2H, s); m/z (M+1)+254.

Workup

  1. filtrationthe accumulated black solid collected by filtration
  2. customchromatographed

Sources & evidence

ORD record
ord-3e4cb691fb41484f9366b95ab70f4b13
Source dataset
uspto-grants-2001_01
Patent number
US06174889B1

Reaction notes

Loading…