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

HRID 1422945노트

반응식

HRID 1422945 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4bd5d85cc64c49588f4e0753ddfb16f0
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927541B2

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