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

HRID 16022

反応式

HRID 16022 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamide収率 97%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-62bc40f4074643f5a8f11e7706291891
出典データセット
uspto-grants-2010_06
特許番号
US07732604B2

関連ノート

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