Ammonium Acetate → HCID 13186946, compound

HRID 2085334Notes

Reaction equation

HRID 2085334 reaction equation
[O:1]=[C:2]1[C:7]2[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9]O[C:6]=2[CH2:5][CH:4]([CH3:16])[CH2:3]1.C([O-])(=O)C.[NH4+:21]>CN(C=O)C>[O:1]=[C:2]1[CH2:3][CH:4]([CH3:16])[CH2:5][C:6]2[NH:21][CH:9]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:7]1=2

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 12051603HCID 12051603, compound

Product 1

HCID 13186946HCID 13186946, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of ethyl 4-oxo-6-methyl-4,5,6,7-tetrahydrobenzofuran-3-carboxylate (15.7 g, 71 mmol) and ammonium acetate (9.54 g, 124 mmol) in N,N,-dimethylformamide (75 mL) was heated at 100° C. for 2 hour The reaction mixture was concentrated in vacuo, ice water was added, and the precipitate collected, rinsed with water then diethyl ether and dried to give ethyl 4-oxo-6-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (5.94 g). To this ester was added aqueous 5N sodium hydroxide (50 mL) and ethyl alcohol (10 mL) and the mixture heated at reflux for 40 minutes. The reaction mixture was cooled in an ice water bath, acidified with aqueous hydrochloric acid, and the precipitate collected, rinsed with water then diethyl ether and dried to give 4-oxo-6-methyl-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (5.2 g). m.p. 210-211° C.

Workup

  1. concentrationwas concentrated in vacuo, ice water
  2. additionwas added
  3. customthe precipitate collected
  4. washrinsed with water
  5. dry with materialdiethyl ether and dried

Sources & evidence

ORD record
ord-18f46d4422bd4a1093c3f288fbe2a914
Source dataset
uspto-grants-2004_04
Patent number
US06720339B2

Reaction notes

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