Acetamide → 6-Chloroquinolin-2-amine

HRID 2202394Notes

Reaction equation

HRID 2202394 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:12])[CH:8]=2)[N:3]=1.C([NH2:16])(=O)C.C([O-])([O-])=O.[K+].[K+]>>[Cl:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:16])[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 178AcetamideHCID 11430Potassium CarbonateHCID 6075022,6-Dichloroquinoline2×

Product 1

HCID 140674256-Chloroquinolin-2-amineYield 98.5%

Conditions

Temperature
200 °C

Procedure

A mixture of 2,6-dichloroquinoline (500 mg, 2.5 mmol), acetamide (3 g, 50.8 mmol) and K2CO3 (1.75 g, 12.7 mmol) in a round bottom flask was stirred at 200° C. for 1.5 hours until TLC indicated that 2,6-dichloroquinoline was consumed. The resulting mixture was cooled to room temperature, and was partitioned between dichloromethane and H2O, the organic layer was dried over anhydrous Na2SO4, concentrated, and the residue was purified by a standard method to give 440 mg of the title compound. LCMS (m/z): 179.7 (M+1)+

Workup

  1. customwas consumed
  2. temperatureThe resulting mixture was cooled to room temperature
  3. customwas partitioned between dichloromethane and H2O
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by a standard method

Sources & evidence

ORD record
ord-3e703f9959024886a7008cd725b67890
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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