Ethanol → 3-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzoic acid

HRID 1091809ノート

反応式

HRID 1091809 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=C([CH:18]=[C:19]([F:21])[CH:20]=1)C#N)=[N:9][NH:8][C:7]2=[O:22].[OH-:23].[K+].[CH2:25]([OH:27])[CH3:26]>O>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][C:13]1[CH:14]=[C:26]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:25]([OH:23])=[O:27])=[N:9][NH:8][C:7]2=[O:22]

参加物

5

反応物 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 577918013-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzonitrile

生成物 1

HCID 577917753-((8-Chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzoic acid収率 96%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

3-((8-chloro-4-oxo-3,4-dihydrophthalazin-1-yl)methyl)-5-fluorobenzonitrile (127) (1.26 g, 4.02 mmol) and potassium hydroxide (2.253 g, 40.16 mmol) were added to ethanol (30 mL) and water (70 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 compound as a beige solid (1.280 g, 96% yield); 1H NMR (400.132 MHz, DMSO) δ 4.69 (2H, s), 7.35 (1H, d), 7.50 (1H, d), 7.58 (1H, s), 7.82 (1H, t), 7.99 (1H, d), 8.34 (1H, d), 12.87 (1H, s); m/z (LC-MS, ESI+), RT=0.99 (M+H 333).

後処理

  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

出典と根拠

ORDレコード
ord-30fe82f3ead7408e927b7bb1a2dd14be
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

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