Acetamide → 4-Aminoquinoline

HRID 1631822Notes

Reaction equation

HRID 1631822 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-033f01f5db1a43cd98ede2009b0fd3c9
Source dataset
uspto-grants-2014_07
Patent number
US08791275B2

Reaction notes

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