Acetamide → 6-Chloroquinolin-2-amine

HRID 514858Notes

Reaction equation

HRID 514858 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-f129f5d84519442e989db335c55789f1
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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