Acetamide → 4-Aminoquinoline

HRID 391367

Reaction equation

HRID 391367 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([NH2:15])(=O)C.C([O-])([O-])=O.[K+].[K+]>>[NH2:15][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 691404-Chloroquinoline

Product 1

HCID 684764-AminoquinolineYield 60.1%

Procedure

A mixture of 4-chloroquinoline (486 mg, 3 mmol), acetamide (2.13 g, 36 mmol) and K2CO3 (2.9 g, 21 mmol) was thoroughly vortexed on a mixer and subjected to microwave irradiation at 175° C. for 1 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic extracts were washed with water and brine and dried over anhydrous Na2SO4. The solvent was removed in vacuo to yield 4-aminoquinoline as a brown solid (260 mg, 60%). EIMS m/z: 145 ([M+1]+).

Workup

  1. customirradiation at 175° C. for 1 h
  2. custompartitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cf00009e451347f09645ee6e5a515002
Source dataset
uspto-grants-2013_02
Patent number
US08383836B2

Linked notes

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