Oxalyl chloride → N-Methoxy-N-methylquinoline-6-carboxamide

HRID 40324

反応式

HRID 40324 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(Cl)(=O)C(Cl)=O.CCN(C(C)C)C(C)C.Cl.[CH3:30][O:31][NH:32][CH3:33]>CN(C=O)C.C(Cl)Cl>[CH3:30][O:31][N:32]([CH3:33])[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 4

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 825716-Quinolinecarboxylic acid

生成物 1

HCID 55211172N-Methoxy-N-methylquinoline-6-carboxamide収率 95.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A 250 mL RB flask was charged with quinoline-6-carboxylic acid (5.00 g, 28.9 mmol), DCM (100 ml, 1554 mmol), oxalyl chloride (3.79 ml, 43.3 mmol), and a few drops of DMF and stirred at RT for 2 hours, then concentrated. The residue was taken up in DCM (100 ml, 1554 mmol), cooled to 0° C., then Hunig's Base (17.7 ml, 101 mmol) and N-methoxymethanamine hydrochloride (2.96 g, 30.3 mmol) were added slowly. The mixture was stirred at room temperature for 16 hours (91463-3-1). The mixture was diluted with DCM (200 mL), then washed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL). The organic layer was dried with MgSO4, filtered, and concentrated to give a brown oil, which was purified by MPLC eluting with 2-6% MeOH/DCM to give N-methoxy-N-methylquinoline-6-carboxamide (5.943 g, 95.2% yield) as a brown oil.

後処理

  1. concentrationconcentrated
  2. temperaturecooled to 0° C.
  3. washwashed with water (250 mL), sat. NaHCO3 (250 mL), and brine (250 mL)
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil, which
  8. customwas purified by MPLC
  9. washeluting with 2-6% MeOH/DCM

出典と根拠

ORDレコード
ord-1c22e723dddd4c25b16eeb5f4c0677ad
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

関連ノート

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