Phenylacetic Acid → HCID 178526479, compound

HRID 1936747Notes

Reaction equation

HRID 1936747 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-4a6b803d8e53478d86f64ae4aff8f577
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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