Dichloromethane → 4-Chloro-6-methoxyquinoline-3-carboxamide

HRID 638969Notes

Reaction equation

HRID 638969 reaction equation
BrC1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([OH:16])=O.C(Cl)(=O)C(Cl)=O.[NH4+:23].[OH-].[CH2:25]([Cl:27])Cl>>[Cl:27][C:25]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:14]([NH2:23])=[O:16]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 684531854-Bromo-6-methoxyquinoline-3-carboxylic acid

Product 1

HCID 221702744-Chloro-6-methoxyquinoline-3-carboxamide

Conditions

Temperature
0 °C

Procedure

To a suspension of dried 4-bromo-6-(methyloxy)-3-quinolinecarboxylic acid (1.4 g, 5 mmol) in CH2Cl2 (20 mL) at 0° C. was added oxalyl chloride (2M in CH2Cl2, 5.0 mL, 10 mmol). After 1 h, an aliquot was quenched with NH4OH and LCMS indicated desired product was formed. Excess NH4OH (2 mL) was slowly added to the reaction solution, maintained at 0° C. (very exothermic), and the reaction was stirred an additional 2 h. The product was isolated via filtration to give 1.0 g (83%).

Workup

  1. customan aliquot was quenched with NH4OH and LCMS
  2. customwas formed
  3. customThe product was isolated via filtration
  4. customto give 1.0 g (83%)

Sources & evidence

ORD record
ord-d0fc8191907646d498e83ec4286269e4
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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