1,1'-Carbonyldiimidazole → N-Methoxy-N-methylquinoline-6-carboxamide

HRID 69153

Reaction equation

HRID 69153 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[N:13]1[C:22]2[C:17](=[CH:18][C:19]([C:23]([OH:25])=O)=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.Cl.[CH3:27][NH:28][O:29][CH3:30]>CN(C=O)C.[Cl-].[Na+].O>[CH3:30][O:29][N:28]([CH3:27])[C:23]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:13]=[CH:14][CH:15]=[CH:16]2)=[O:25]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 825716-Quinolinecarboxylic acid

Product 1

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

CDI (25.8 g, 151 mmol) was added to a solution of 6-quinolinecarboxylic acid (25 g, 141 mmol) in DMF and the mixture stirred at rt for 10 min. N,O-dimethylhydroxylamine hydrochloride (14.1 g, 142 mmol) was added and the mixture stirred for an additional hour. Brine was then added and the mixture extracted with EtOAc. The organic extracts were dried, filtered and concentrated to give the title compound as a yellow oil (tR 0.2 min (conditions 2), MH+=217).

Workup

  1. stirringthe mixture stirred for an additional hour
  2. extractionthe mixture extracted with EtOAc
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d58dd5c6c0d64436a5bc7b0ccefe5c80
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Linked notes

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