Sodium Hydroxide → HCID 44125248, compound

HRID 601940Notes

Reaction equation

HRID 601940 reaction equation
[CH2:1]([CH:8]1[CH2:16][CH2:15][CH2:14][C:13]2[NH:12][C:11]([C:17]([O:19]C)=[O:18])=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>>[CH2:1]([CH:8]1[CH2:16][CH2:15][CH2:14][C:13]2[NH:12][C:11]([C:17]([OH:19])=[O:18])=[CH:10][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 57435168HCID 57435168, compound

Product 1

HCID 44125248HCID 44125248, compoundYield 93%

Procedure

The title compound was synthesized from methyl 4-benzyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (20 mg, 0.08 mmol) and aqueous NaOH (1M in H2O, 0.8 mL, 0.8 mmol) according to General Procedure 7. The solid was filtered off, washed with water and dried under vacuum for about 12 h to give 4-benzyl-4,5,6,7-tetrahydro-1H-indole-2-carboxylic acid (32) (19 mg). 1H NMR (CHLOROFORM-d 400 MHz) δ ppm 8.8 (1H, br s), 7.3-7.33 (2H, m), 7.2-7.26 (3H, m), 6.81 (1H, s), 3.09 (1H, dd), 2.9 (1H, m), 2.55-2.65 (3H, m), 1.9-2.0 (1H, m), 1.6-1.8 (2H, m), 1.3-1.4 (1H, m); LC/MS: 89%, m/z=255

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water
  3. customdried under vacuum for about 12 h

Sources & evidence

ORD record
ord-a53dd0f7b1ac45c480a6bc88685e3bda
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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