Potassium Hydroxide → 8-Fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid

HRID 1476811노트

반응식

HRID 1476811 반응식
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8](/[CH:12]=[C:13]2\[N:14]=C(C3C=CC=CC=3)[O:16][C:17]\2=[O:18])[C:3]=1[C:4](OC)=[O:5].[OH-].[K+]>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:5])[NH:14][C:13]([C:17]([OH:16])=[O:18])=[CH:12]2

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 90387079(Z)-methyl 2-fluoro-6-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzoate

생성물 1

HCID 903871878-Fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid수율 41.9%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

A solution of crude (Z)-methyl 2-fluoro-6-((5-oxo-2-phenyloxazol-4(5H)-ylidene)methyl)benzoate (15 g) and potassium hydroxide (2.58 g, 46 mmol) in acetic anhydride (150 mL) was heated at 100° C. for 2 hours. The solvent was removed in vacuo, and the residue was diluted with water (30 mL). The resulting mixture was neutralized with 1M aqueous HCl (100 mL) and filtered. The solids were dried in vacuo to give 8-fluoro-1-oxo-1,2-dihydroisoquinoline-3-carboxylic acid (4 g, ESI-MS m/z [M+H]+ 208.0) which was converted to the methyl ester as described, below. The filtrate was concentrated under reduced pressure to give crude product which was purified by column chromatography eluting with a gradient of EtOAc (30-100%) and PE to give a first batch of the title compound (2 g, 19.6%). ESI-MS m/z [M+H]+=222.1.

후처리

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with water (30 mL)
  3. filtrationfiltered
  4. customThe solids were dried in vacuo

출처 및 근거

ORD 기록
ord-e6a5362e53c34fdca6ec09ab17b4b5e3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09402841B2

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