N,O-Dimethylhydroxylamine → N-Methoxy-N-methylquinoline-6-carboxamide

HRID 16022

Reaction equation

HRID 16022 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[CH3:26][NH:27][O:28][CH3:29]>CN(C=O)C.CCOC(C)=O.O>[CH3:29][O:28][N:27]([CH3:26])[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[CH:4]2)=[O:13]

Participants

7

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 825716-Quinolinecarboxylic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamideYield 97%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of quinoline-6-carboxylic acid (10 g, 57.75 mmol) in DMF (200 mL) was added carbonyl diimidazole (10.3 g, 62.5 mmol) under nitrogen. The reaction was stirred for 1 hour. To the solution was added N,O-dimethyl hydroxylamine (5.6 g, 57.75 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was diluted with EtOAc (150 mL) and water (150 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (5×100 mL). The organics were combined and washed with water (3×100 mL), brine (2×100 mL), dried over Na2SO4, filtered and concentrated to give quinoline-6-carboxylic acid methoxy-methyl-amide (11.97 g, 97% yield).

Workup

  1. stirringthe reaction was stirred at ambient temperature for 16 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (5×100 mL)
  4. washwashed with water (3×100 mL), brine (2×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-62bc40f4074643f5a8f11e7706291891
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

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