Thionyl Chloride → 2-Chloro-6-methoxyquinoline-3-carbonitrile

HRID 2073774

Reaction equation

HRID 2073774 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:15]([CH:16]=[N:17]O)=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1>CN(C)C=O>[Cl:5][C:6]1[C:15]([C:16]#[N:17])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:19][CH3:20])[CH:12]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 24874202-Chloro-6-methoxy-3-quinolinecarboxaldehyde oxime

Product 1

HCID 8656122-Chloro-6-methoxyquinoline-3-carbonitrileYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (7.9 ml) was added dropwise over a 12 min period to a stirred solution of 16.3 g 2-chloro-6-methoxy-3-quinolinecarboxaldehyde oxime in 160 ml dimethylformamide at 0° C. The reaction mixture was stirred for 15 min longer at 0° C. and then at room temperature overnight. The mixture was then quenched in ice-water, and the yellow solid product was collected, washed with water and dried in vacuo at 75° C. to give 14.8 g 2-chloro-6-methoxy-3-quinolinecarbonitrile, m.p. 201°-202° C.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was then quenched in ice-water
  4. customthe yellow solid product was collected
  5. washwashed with water
  6. customdried in vacuo at 75° C.

Sources & evidence

ORD record
ord-0ec2b8ce49ca4ef49a5098f14f53663d
Source dataset
uspto-grants-1990_04
Patent number
US04920128

Linked notes

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