Sodium Hydroxide → 3-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide

HRID 1422971ノート

反応式

HRID 1422971 の反応式
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]#[N:13])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.[OH-:16].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12]([NH2:13])=[O:16])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 672545843-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile

生成物 1

HCID 672571323-Chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide収率 64%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

3-Chloro-6-methoxy-[1,5]naphthyridine-4-carbonitrile (5.0 g, 22.8 mmol, 1.0 eq) is suspended in a 10% sodium hydroxide aqueous solution (125 mL) and the resulting mixture is heated to reflux for 30 minutes. The reaction mixture is then extracted with ethyl acetate (3×100 mL) and the pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to give the crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:1 to 4:1, v/v) to afford 3-chloro-6-methoxy-[1,5]naphthyridine-4-carboxylic acid amide as an off-white solid (3.44 g, 64% yield).

後処理

  1. temperaturethe resulting mixture is heated
  2. temperatureto reflux for 30 minutes
  3. extractionThe reaction mixture is then extracted with ethyl acetate (3×100 mL)
  4. additionthe pH is adjusted to 3-4 by the addition of a 3N hydrochloric acid aqueous solution
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product that
  9. customis purified by column chromatography (silica gel, eluent

出典と根拠

ORDレコード
ord-003dbd83e09141a9b6f2eb4c31049521
出典データセット
uspto-grants-2015_01
特許番号
US08927541B2

反応ノート

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