Ethanol → 2-Fluoro-5-[(8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid

HRID 1091805노트

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HRID 1091805 반응식
[F:1][C:2]1C=[CH:8][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:21][CH3:22])[C:14](=[O:23])[NH:13][N:12]=2)=[CH:6][C:3]=1C#N.[OH-:24].[K+].[CH2:26]([OH:28])[CH3:27]>O>[F:1][C:2]1[CH:3]=[CH:6][C:7]([CH2:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][C:19]=3[O:21][CH3:22])[C:14](=[O:23])[NH:13][N:12]=2)=[CH:8][C:27]=1[C:26]([OH:24])=[O:28]

참가 물질

5

반응물 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 577918302-Fluoro-5-((8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile

생성물 1

HCID 577918172-Fluoro-5-[(8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl]benzoic acid수율 83%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

2-fluoro-5-((8-methoxy-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)benzonitrile (124) (2.7 g, 8.73 mmol) and potassium hydroxide (4.90 g, 87.30 mmol) were added to ethanol (20 mL) and water (50 mL) and heated at 100° C. for 5 hours. The ethanol was evaporated off and the aqueous was extracted with ethyl acetate (1×75 mL). The aqueous was then acidified to pH1 with conc HCl to afford a solid, this was filtered, washed with water and dried to afford the desired material as a white solid (2.370 g, 83%); 1H NMR (400.132 MHz, DMSO) δ 3.82 (3H, s), 4.40 (2H, s), 7.16-7.23 (1H, m), 7.40-7.46 (2H, m), 7.64-7.68 (1H, m), 7.76 (1H, t), 7.84-7.88 (1H, m), 12.96-13.28 (1H, m), 12.59-12.63 (1H, m).

후처리

  1. customThe ethanol was evaporated off
  2. extractionthe aqueous was extracted with ethyl acetate (1×75 mL)
  3. customto afford a solid
  4. filtrationthis was filtered
  5. washwashed with water
  6. customdried

출처 및 근거

ORD 기록
ord-8ee2403203234e69b5588cc0415b7e40
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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