Phenylacetic Acid → N-[2-(1H-Indol-2-yl)phenyl]-2-phenylacetamide

HRID 1272448Notes

Reaction equation

HRID 1272448 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[C:17]1([CH2:23][C:24](O)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:24](=[O:25])[CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 999Phenylacetic AcidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 18455775N-[2-(1H-Indol-2-yl)phenyl]-2-phenylacetamideYield 62%

Procedure

Prepared from 2-(2-aminophenyl) indole and phenylacetic acid in 62% yield following procedure 1. The product was crystallized from methanol. 100% Purity by LC/MS (230 DAD), Mass-spec [M+H+]=327, 1H NMR (MeOH-d4): 3.69 s (2H), 6.21 s (1H), 7.03 t, 7 Hz (1H), 7.12 t, 8 Hz (1H), 7.21–7.28 m (6H), 7.33–7.36 m (2H), 7.46 d, 8 Hz (1H), 7.54 dd, 7.1 Hz (1H), 7.89 d, 8 Hz (1H).

Workup

  1. customThe product was crystallized from methanol
  2. customby LC/MS (230 DAD), Mass-spec [M+H+]=327, 1H NMR (MeOH-d4): 3.69 s (2H), 6.21 s (1H), 7.03 t, 7 Hz (1H), 7.12 t, 8 Hz (1H), 7.21–7.28 m (6H), 7.33–7.36 m (2H), 7.46 d, 8 Hz (1H), 7.54
  3. custom7.1 Hz (1H), 7.89 d, 8 Hz (1H)

Sources & evidence

ORD record
ord-8bcf5550b5224ff1a9c11b45601fa3fa
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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