Protocatechuic Acid → HCID 10337546, compound

HRID 1272446Notes

Reaction equation

HRID 1272446 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:19]=[C:20]([CH:24]=[CH:25][C:26]=1[OH:27])[C:21](O)=[O:22]>>[OH:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[OH:27])[C:21]([NH: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)=[O:22]

Participants

3

Reactant 2

HCID 72Protocatechuic AcidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 10337546HCID 10337546, compoundYield 54%

Procedure

Prepared from 2-(2-aminophenyl) indole and 3,4-dihydroxybenzoic acid in 54% yield following procedure 1. The product was chromatographed on silica. 100% Purity by LC/MS (230 DAD), Mass-spec (M+H+)=345.83, 1H NMR (MeOH-d4): 6.645 s (1H), 6.80 d, 8 Hz (1H), 7.02 t, 8 Hz (1H), 7.12 td, 8.1 Hz (1H), 7.23 dd, 8.1 Hz (1H), 7.33–7.36 m (2H), 7.39–7.42 m (2H), 7.52 d, 7 Hz (1H), 7.65 dd, 8.1 Hz (1H), 7.94 d, 8 Hz (1H).

Workup

  1. customThe product was chromatographed on silica
  2. custom8 Hz (1H), 7.02 t, 8 Hz (1H), 7.12 td, 8.1 Hz (1H), 7.23 dd, 8.1 Hz (1H), 7.33–7.36 m (2H), 7.39–7.42 m (2H), 7.52 d, 7 Hz (1H), 7.65
  3. custom8.1 Hz (1H), 7.94 d, 8 Hz (1H)

Sources & evidence

ORD record
ord-7e1c36583d4449ec9e4259103ebf3c75
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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