Ammonium Acetate → HCID 13186946, compound

HRID 276125Notes

Reaction equation

HRID 276125 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 hours. 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. concentrationThe reaction mixture was 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-ff49c214f0c44d85af8cc681719bec6a
Source dataset
uspto-grants-2002_03
Patent number
US06353109B2

Reaction notes

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