8-Hydroxyquinoline → Acetamide, N-(2-methoxyphenyl)-

HRID 1084986

Reaction equation

HRID 1084986 reaction equation
C[O-].[Na+].[OH:4][C:5]1C=CC=C2C=1N=CC=C2.Br[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23](=[O:25])[CH3:24]>CO.[Cu]>[C:23]([NH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:4][CH3:5])(=[O:25])[CH3:24]

Participants

6

Reactant 3

HCID 19238-HydroxyquinolineHCID 1364162'-BromoacetanilideHCID 10942334Sodium Methoxide

Product 1

HCID 7135Acetamide, N-(2-methoxyphenyl)-Yield 866.6%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent2×

Procedure

2.3 ml of a 28% solution of sodium methoxide in methanol and 63 mg of copper powder were added to 40 ml of methanol, and the mixture was heated under reflux for 1 hour. Then, 145 mg of 8-hydroxyquinoline and 2.14 g of 2-bromo-1-acetylaminobenzene were added thereto, and the mixture was heated under reflux for 3 hours. The reaction mixture was treated in a usual manner, to obtain 1.43 g (yield: 87%) of the desired compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 3 hours
  5. additionThe reaction mixture was treated in a usual manner

Sources & evidence

ORD record
ord-e8e0abe2a99d4208807a76251ef34c06
Source dataset
uspto-grants-1991_04
Patent number
US05006660

Linked notes

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