Dimethylformamide → 2-Methoxyquinoline-6-carboxylic acid amide

HRID 986022Notes

Reaction equation

HRID 986022 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([OH:21])=O)[CH:15]=2)[N:10]=1.C[N:23](C=O)C>ClCCl>[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([NH2:23])=[O:21])[CH:15]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 201589862-Methoxyquinoline-6-carboxylic acid

Product 1

HCID 540381422-Methoxyquinoline-6-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (10.3 cm3) was added dropwise to a stirred solution of 2-methoxyquinoline-6-carboxylic acid (12.0 g) in dichloromethane (100 cm3) and DMF (0.1 g) at 0°. The mixture was warmed to room temperature and after 2 hours volatile material was removed in vacuo. The residue was taken into dichloromethane (100 cm3), cooled to 0° and treated cautiously with aqueous ammonia solution (30 cm3 of S.G. 0.880). After 2 hours the mixture was concentrated in vacuo and the solid residue was recrystallised from isopropanol to afford 2-methoxyquinoline-6-carboxylic acid amide, m.p. 212°-214°, (7.9 g).

Workup

  1. customwas removed in vacuo
  2. temperaturecooled to 0°
  3. additiontreated cautiously with aqueous ammonia solution (30 cm3 of S.G. 0.880)
  4. concentrationAfter 2 hours the mixture was concentrated in vacuo
  5. customthe solid residue was recrystallised from isopropanol

Sources & evidence

ORD record
ord-fae9b9d2a32245c083df18350094dc12
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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