Ammonia → 4-(1-Amino-3-anilino-1,3-dioxopropan-2-yl)benzoic acid

HRID 1694843Notes

Reaction equation

HRID 1694843 reaction equation
[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12]C1C=CC=CC=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N>>[NH2:12][C:10](=[O:11])[CH:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=1)[C:8]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:28]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 593764614-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

Product 1

HCID 593764434-(1-Amino-3-anilino-1,3-dioxopropan-2-yl)benzoic acid

Procedure

A solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (0.25 g, 0.67 mmol) in 7.0 N methanolic ammonia (1.9 mL, 13.4 mmol) in a sealed tube was heated to 160° C. for 1 hour in the microwave. The reaction was concentrated in vacuo and purified by reverse phase HPLC (15-75% MeCN/H2O with 0.05% TFA) to give the title compound as a white solid. 1H NMR (600 MHz, DMSO-d6) δ 12.90 (bs, 1H), 10.28 (s, 1H), 7.89 (d, J=8.5 Hz, 2H), 7.55 (m, 3H), 7.52 (d, J=8.5 Hz, 2H), 7.35 (bs, 1H), 7.27 (t, J=8.1 Hz, 2H), 7.03 (t, J=7.5 Hz, 1H), 4.66 (s, 1H); ESIMS calcd 299.0 (M++H), found 299.0 (M++H).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by reverse phase HPLC (15-75% MeCN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-7c93cfff77024213a3c1f8553b41e905
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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