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

HRID 1476811ノート

反応式

HRID 1476811 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e6a5362e53c34fdca6ec09ab17b4b5e3
出典データセット
uspto-grants-2016_08
特許番号
US09402841B2

反応ノート

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