Ammonium Hydroxide → methyl 2-carbamoyl-1H-indole-5-carboxylate

HRID 2403669Notes

Reaction equation

HRID 2403669 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]([OH:16])=O)=[CH:8]2)=[O:4].[OH-].[NH4+:18]>O1CCCC1>[C:14]([C:9]1[NH:10][C:11]2[C:7]([CH:8]=1)=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:13][CH:12]=2)(=[O:16])[NH2:18]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 529879165-(methoxycarbonyl)-1H-indole-2-carboxylic acid

Product 1

HCID 70896052methyl 2-carbamoyl-1H-indole-5-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(methoxycarbonyl)-1H-indole-2-carboxylic acid (2.50 g, 11.4 mmol) in tetrahydrofuran (20 mL) was added 1,1-carbonyldiimidazole (3.70 g, 22.8 mmol). The yellow suspension was stirred for 2 hours. Then concentrated ammonium hydroxide (20 mL) was added and the mixture was stirred at room temperature for 5 hours. The pale green suspension was filtered, washed with water and 5 mL of methanol, and air dried to give methyl 2-carbamoyl-1H-indole-5-carboxylate (2.04 g, 82%) as a colorless solid. 1H NMR (400 MHz, DMSO-d6, δ): 11.93 (br. s., 1 H), 8.32 (d, J=1.2 Hz, 1 H), 8.06 (br. s., 1 H), 7.79 (dd, J=8.6, 1.6 Hz, 1 H), 7.48 (d, J=8.6 Hz, 1 H), 7.45 (br. s., 1 H), 7.27 (s, 1 H), 3.32 (s, 3 H).

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. filtrationThe pale green suspension was filtered
  3. washwashed with water and 5 mL of methanol, and air
  4. customdried

Sources & evidence

ORD record
ord-2830a91992e74657bd291bef985fdc02
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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