4-Hydroxybenzoic Acid → 4-Hydroxy-N-(2-(1H-indol-2-yl)-phenyl)-benzamide

HRID 1272445Notes

Reaction equation

HRID 1272445 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.[OH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1>>[OH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:23])=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 1354-Hydroxybenzoic AcidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 184557184-Hydroxy-N-(2-(1H-indol-2-yl)-phenyl)-benzamide

Procedure

Prepared from 2-(2-aminophenyl) indole and 4-hydroxybenzoic acid in 35% overall yield following procedure 1. The product was chromatographed on silica and crystallized from acetonitrile. 95.6% Purity by LC/MS (230 DAD) Mass-spec (M+H+)=329.8 1H NMR (MeOH-d4): 6.65 s (1H), 6.83 m (2H), 7.01 t, 7 Hz (1H), 7.12 td, 7.1 Hz (1H), 7.34 td, 7.1 Hz (1H), 7.39–7.43 m (2H), 7.51 d, 7 Hz (1H), 7.66 dd, 8.1 Hz (1H), 7.76 m (2H), 7.91 dd, 8.1 Hz (1H).

Workup

  1. customoverall yield
  2. customThe product was chromatographed on silica
  3. customcrystallized from acetonitrile
  4. customby LC/MS (230 DAD) Mass-spec (M+H+)=329.8 1H NMR (MeOH-d4): 6.65 s (1H), 6.83 m (2H), 7.01 t, 7 Hz (1H), 7.12 td, 7.1 Hz (1H), 7.34 td, 7.1 Hz (1H), 7.39–7.43 m (2H), 7.51 d, 7 Hz (1H), 7.66

Sources & evidence

ORD record
ord-56928689d19444d3a74cd8184dac0ed3
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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