Hydrochloric Acid → HCID 12051604, compound

HRID 276126Notes

Reaction equation

HRID 276126 reaction equation
[O:1]=[C:2]1[CH2:10][CH:9]([CH3:11])[CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:12]([O:14]CC)=[O:13])[C:3]1=2.[OH-].[Na+].Cl>C(O)C>[O:1]=[C:2]1[CH2:10][CH:9]([CH3:11])[CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:12]([OH:14])=[O:13])[C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13186946HCID 13186946, compound

Product 1

HCID 12051604HCID 12051604, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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. temperaturethe mixture heated
  2. temperatureat reflux for 40 minutes
  3. temperatureThe reaction mixture was cooled in an ice water bath
  4. customthe precipitate collected
  5. washrinsed with water
  6. dry with materialdiethyl ether and dried

Sources & evidence

ORD record
ord-87cab5ec4b3e4d2897d98bb5d12ceb69
Source dataset
uspto-grants-2002_03
Patent number
US06353109B2

Reaction notes

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