Sodium Hydroxide → 1-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid

HRID 2077211노트

반응식

HRID 2077211 반응식
C[O:2][C:3]([C:5]1[N:6]=[C:7]([C:24]#[N:25])[C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:4].[OH-].[Na+]>CO.O1CCCC1>[C:24]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([O:15][CH3:16])=[C:5]([C:3]([OH:4])=[O:2])[N:6]=1)#[N:25]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 671104881-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester

생성물 1

HCID 671101241-Cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid수율 92.7%

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a mixture of 1-cyano-4-methoxy-8-phenoxy-isoquinoline-3-carboxylic acid methyl ester (727 mg, 2.18 mmol) and methanol/tetrahydrofuran (12.5 mL, 1:1.5) was added 2N sodium hydroxide (5.4 mL, 10.89 mmol) at room temperature. The yellow solution was stirred at that temperature for seventy minutes before it was concentrated. Water (20 mL) was added and the mixture was adjusted to pH=2 with 1N HCl (13 mL). The mixture was then extracted with dichloromethane and ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo to give the title compound as a yellow solid (647 mg): MS: (+) m/z 320.80 (M+1).

후처리

  1. concentrationwas concentrated
  2. additionWater (20 mL) was added
  3. extractionThe mixture was then extracted with dichloromethane and ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f650121e5c714e178c33d18a7b9fa2cb
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928120B2

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