Sodium Hydroxide → 3-(Aminocarbonyl)-1H-indole-5-carboxylic acid

HRID 2403672Notes

Reaction equation

HRID 2403672 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14]CC)=[O:13])[CH:10]=2)[NH:5][CH:4]=1)#[N:2].OO.NC(N)=[O:21].[OH-].[Na+]>CO.O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[NH:5][CH:4]=1)(=[O:21])[NH2:2]

Participants

6

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 31294Carbamide PeroxideHCID 70896040HCID 70896040, compound

Product 1

HCID 684318393-(Aminocarbonyl)-1H-indole-5-carboxylic acidYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 3-cyano-1H-indole-5-carboxylate (1.05 g, 4.89 mmol) in methanol (12 mL) was added to a 0° C. solution of urea hydrogen peroxide (4.74 g, 48.9 mmol) and sodium hydroxide (11.7 mL of a 2.5 M solution in water, 29.3 mmol). The mixture was allowed to warm to room temperature and stir overnight. An additional 2 mL of a 2.5 M solution of sodium hydroxide was added and the reaction was left stirring 4 hours. The mixture was concentrated and acidified to pH 2 using 6 M hydrochloric acid. The resulting precipitate was filtered off and dried under vacuum at 60° C. to give the title compound (915 mg, 92%). 1H NMR (400 MHz, DMSO-d6, δ): 12.46 (br. s., 1 H), 11.84 (s, 1 H), 8.85 (s, 1 H), 8.12 (d, J=2.5 Hz, 1 H), 7.75 (dd, J=8.6, 1.6 Hz, 1 H), 7.50-7.63 (m, 1 H), 7.47 (d, J=8.6 Hz, 1 H), 6.88 (br. s., 1 H).

Workup

  1. waitthe reaction was left
  2. stirringstirring 4 hours
  3. concentrationThe mixture was concentrated
  4. filtrationThe resulting precipitate was filtered off
  5. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-f6976150b16747a79aa5853b48017c65
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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