Chloroform → N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamide

HRID 901942Notes

Reaction equation

HRID 901942 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[N:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:3])[CH3:2].C(Cl)(Cl)Cl>C(O)(=O)C>[C:1]([NH:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 79448Acetamide, N-3-quinolinyl-

Product 1

HCID 19697545N-(1,2,3,4-tetrahydroquinolin-3-yl)acetamideYield 55.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Borane-pyridine complex (320 mg, 3.5 mmol) was added to a solution of 3-acetamidoquinoline (320 mg, 1.7 mmol) in acetic acid (20 ml) and the mixture was stirred at room temperature for 18 h. Chloroform (150 ml) was added and the mixture was washed with 2N sodium hydroxide solution, water and brine. The organic phase was dried and reduced. Chromatography (80% EtOAc/20% 60-80 pet. ether) afforded 3-acetamido-1,2,3,4-tetrahydroquinoline (180 mg, 55%) as a pale yellow solid.

Workup

  1. washthe mixture was washed with 2N sodium hydroxide solution, water and brine
  2. customThe organic phase was dried

Sources & evidence

ORD record
ord-9ad550024e81472dbea69b2c7a2f0b65
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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