Dimethylformamide → 4-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrile

HRID 1935030Notes

Reaction equation

HRID 1935030 reaction equation
[CH2:1]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=O)[C:9]([C:14]#[N:15])=[CH:10][NH:11]2)=[CH:6][C:5]=1[O:17][CH3:18])[CH3:2].C(Cl)(=O)C([Cl:22])=O.CN(C=O)C.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+].C(Cl)Cl>[Cl:22][C:8]1[C:7]2[C:12](=[CH:13][C:4]([O:3][CH2:1][CH3:2])=[C:5]([O:17][CH3:18])[CH:6]=2)[N:11]=[CH:10][C:9]=1[C:14]#[N:15]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 65578Oxalyl chlorideHCID 104904723-Quinolinecarbonitrile, 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-

Product 1

HCID 105634734-Chloro-7-ethoxy-6-methoxy-3-quinolinecarbonitrileYield 89.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Mixed 122 mg (0.50 mmol) 7-ethoxy-1,4-dihydro-6-methoxy-4-oxo-3-quinolinecarbonitrile and 2.0 ml methylene chloride under N2 and kept temperature near 25° C. Added 218 μl (2.5 mmol) oxalyl chloride and 10 μl (0.125 mmol) DMF. Stirred overnight, diluted with chloroform and stirred in saturated sodium bicarbonate until basic. Separated layers and dried organics with magnesium sulfate, stripped solvent and dried in vacuo, giving 117 mg of tan solid: mass spectrum (electrospray m/e): M+H=262.8, 264.8.

Workup

  1. customnear 25° C
  2. customdried in vacuo

Sources & evidence

ORD record
ord-d1c9290b9ee34a7bb5392bdb1686107f
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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