Benzo-1,3-dioxole-5-acetic acid → HCID 18455696, compound

HRID 1272452Notes

Reaction equation

HRID 1272452 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.[CH2:17]1[O:21][C:20]2[CH:22]=[C:23]([CH2:26][C:27](O)=[O:28])[CH:24]=[CH:25][C:19]=2[O:18]1>>[O:18]1[C:19]2[CH:25]=[CH:24][C:23]([CH2:26][C:27]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]3[NH:9][C:10]4[C:15]([CH:16]=3)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:28])=[CH:22][C:20]=2[O:21][CH2:17]1

Participants

3

Reactant 2

HCID 76115Benzo-1,3-dioxole-5-acetic acidHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 18455696HCID 18455696, compoundYield 55%

Procedure

Prepared from 2-(2-aminophenyl) indole and 3,4-(methylenedioxy) phenylacetic acid in 55% yield. The product was purified by crystallization from acetonitrile. 100% Purity by LC/MS (230 DAD), Mass-spec [M+H+]=371, 1H NMR (MeOH-d4): 3.61 s (2H), 5.82 s (2H), 6.20 s (1H), 6.66 d, 8 Hz (1H), 6.74 dd, 8.1 Hz (1H), 6.76 d, 1 Hz (1H), 7.03 t, 8 Hz (1H), 7.12 t, 8 Hz (1H), 7.25 t, 8 Hz (1H), 7.33–7.36 m (2H), 7.48 d, 8 Hz (1H), 7.52 d, 8 Hz (1H), 7.99 d, 8 Hz (1H).

Workup

  1. customThe product was purified by crystallization from acetonitrile
  2. custom8 Hz (1H), 6.74 dd, 8.1 Hz (1H), 6.76 d, 1 Hz (1H), 7.03 t, 8 Hz (1H), 7.12 t, 8 Hz (1H), 7.25 t, 8 Hz (1H), 7.33–7.36 m (2H), 7.48 d, 8 Hz (1H), 7.52 d, 8 Hz (1H), 7.99 d, 8 Hz (1H)

Sources & evidence

ORD record
ord-0bf4d21311f040d6ab71891b19be84c0
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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