Phenylacetic Acid → HCID 178526479, compound

HRID 2306672Notes

Reaction equation

HRID 2306672 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

Conditions

Temperature
110 °C

Procedure

A mixture 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. temperatureThe mixture was cooled to room temperature
  2. filtrationthe accumulated black solid collected by filtration
  3. customchromatographed

Sources & evidence

ORD record
ord-022ba465af0a4f55b37b4e89558083f4
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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