Triethylamine → HCID 73703362, compound

HRID 2307415Notes

Reaction equation

HRID 2307415 reaction equation
[CH3:1][O:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14](=O)[CH3:15])=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].C(N(CC)CC)C.Cl.[OH-:25].[NH4+:26]>C(O)C>[OH:25][N:26]=[C:14]([C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:6][CH2:7]2)[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13908798HCID 13908798, compoundHCID 20744325Methyl 5-acetyl-2,3-dihydro-1H-indole-1-carboxylate

Product 1

HCID 73703362HCID 73703362, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-acetyl-2,3-dihydroindole-1-carboxylic acid methyl ester, Preparation 18 (6.57 g, 30 mmol), triethylamine (6.06 g, 60 mmol), and ammonium hydroxide hydrochloride (4.2 g, 60 mmol) in ethanol (80 mL) was stirred under reflux for 16 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The residue was extracted with CH2Cl2 (1×60 mL), and the organic layer was dried over anhydrous magnesium sulfate, filtered, and the resultant filtrate was concentrated in vacuo. The crude material was purified by flash column chromatography on silica eluting with ethyl acetate/hexane (30%) to provide the title product (6.3 g, 90%) as a solid.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted with CH2Cl2 (1×60 mL)
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe resultant filtrate was concentrated in vacuo
  7. customThe crude material was purified by flash column chromatography on silica eluting with ethyl acetate/hexane (30%)

Sources & evidence

ORD record
ord-ab04c1934cde41a59b9880e7b3017120
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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