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

HRID 1422945ノート

反応式

HRID 1422945 の反応式
[OH-].[Na+].C([O:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[Cl:18])=[N:15][C:14]([O:19][CH3:20])=[CH:13][CH:12]=2)=[O:7])C>O1CCCC1.O>[Cl:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[N:15]=2)[N:10]=[CH:9][C:8]=1[C:6]([OH:7])=[O:5]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 23209173Ethyl 4-chloro-6-methoxy-1,5-naphthyridine-3-carboxylate

生成物 1

HCID 672555724-Chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid収率 96.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Sodium hydroxide (5.86 g, 140.6 mmol, 2.5 eq) is added protionwise at room temperature to a stirred solution of 4-chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid ethyl ester (15.0 g, 56.25 mmol, 1.0 eq) in tetrahydrofuran (150 mL) and water (80 mL). After 15 hours stirring at room temperature, tetrahydrofuran is removed, the aqueous layer is cooled down to 0° C. and the pH is adjusted to 3 by the addition of a 2N hydrochloric acid aqueous solution. The resulting precipitate is collected by filtration, washed with water and dried under high vacuum to afford 4-chloro-6-methoxy-[1,5]naphthyridine-3-carboxylic acid as a light red solid (12.9 g, 96% yield).

後処理

  1. customtetrahydrofuran is removed
  2. temperaturethe aqueous layer is cooled down to 0° C.
  3. additionthe pH is adjusted to 3 by the addition of a 2N hydrochloric acid aqueous solution
  4. filtrationThe resulting precipitate is collected by filtration
  5. washwashed with water
  6. customdried under high vacuum

出典と根拠

ORDレコード
ord-4bd5d85cc64c49588f4e0753ddfb16f0
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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