3-(4-Hydroxyphenyl)propionic acid → HCID 10383639, compound

HRID 1272454Notes

Reaction equation

HRID 1272454 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:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26](O)=[O:27])=[CH:20][CH:19]=1>>[OH:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][C:26]([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:27])=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 103943-(4-Hydroxyphenyl)propionic acidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 10383639HCID 10383639, compoundYield 55%

Procedure

Prepared from 2-(2-aminophenyl) indole and 3-(4-hydroxyphenyl) propionic acid in 55% yield following procedure 1. The product was chromatographed on silica and crystallized from acetonitrile. 100% Purity by LC/MS (230 DAD), Mass-spec [M+H+]=357, 1H NMR (MeOH-d4): 2.61 t, 7.4 Hz (1H), 2.89 t, 7.4 Hz (1H), 6.37 s (1H), 6.72 d, 8 Hz (2H), 7.00–7.06 m (3H), 7.11 t, 7 Hz (1H), 7.27–7.35 m (2H), 7.38 d, 8 Hz (1H), 7.54 d, 7 Hz (1H), 7.58 dd, 7.1 Hz (1H), 7.67 d, 8 Hz (1H).

Workup

  1. customThe product was chromatographed on silica
  2. customcrystallized from acetonitrile
  3. customby LC/MS (230 DAD), Mass-spec [M+H+]=357, 1H NMR (MeOH-d4): 2.61 t, 7.4 Hz (1H), 2.89 t, 7.4 Hz (1H), 6.37 s (1H), 6.72 d, 8 Hz (2H), 7.00–7.06 m (3H), 7.11 t, 7 Hz (1H), 7.27–7.35 m (2H), 7.38 d, 8 Hz (1H), 7.54 d, 7 Hz (1H), 7.58
  4. custom7.1 Hz (1H), 7.67 d, 8 Hz (1H)

Sources & evidence

ORD record
ord-3136a4b0042240fda12ad6ae98d1f05d
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

Loading…