Sodium Hydroxide → 5-acetamido-1H-indole-2-carboxylic Acid

HRID 1455887Notes

Reaction equation

HRID 1455887 reaction equation
[OH-].[Na+].[NH:3]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([O:18]CC)=[O:17])=[CH:10]2)[C:4]([CH3:6])=[O:5]>CO>[NH:3]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([C:16]([OH:18])=[O:17])=[CH:10]2)[C:4]([CH3:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 685005ethyl 5-acetamido-1H-indole-2-carboxylate

Product 1

HCID 107751705-acetamido-1H-indole-2-carboxylic AcidYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3N NaOH (2 mL) was added to a solution of 3 (250 mg, 1.02 mmol) in methanol (7 mL) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated and water (5 mL) was added. The solution was neutralized to pH 2 using 20% HCl and the precipitate was filtered and washed with water. 4 was obtained as a grey powder (158 mg, 71% yield), mp: 260° C. (dec). 1H NMR (DMSO-d6, ppm): 11.62 (s, 1 H, NH), 9.77 (s, 1 H, NH), 7.98-7.97 (d, 1 H, J=1.4 Hz, Ar--H), 7.36-7.28 (m, 2 H, Ar--H), 7.02 (d, 1 H, J=1.5 Hz, Ar--H), 2.03 (s, 3 H, CH3CO), Anal. (C11H10N2O3 0.6H2O), C, H, N.

Workup

  1. customThe reaction mixture was evaporated
  2. additionwater (5 mL) was added
  3. filtrationthe precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-90c627adde5740e3850db01d5d3c9cd5
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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