Nitric Acid → 5-[(4-fluorophenyl)methyl]-3-nitro-2(1H)-pyridinone

HRID 2364193ノート

反応式

HRID 2364193 の反応式
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:14]=[CH:15][C:16](=[O:19])[NH:17][CH:18]=2)=[CH:8][CH:7]=1.O>C(O)(C(F)(F)F)=O>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][C:13]2[CH:14]=[C:15]([N+:1]([O-:4])=[O:2])[C:16](=[O:19])[NH:17][CH:18]=2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 944Nitric Acid2 回HCID 962WaterHCID 573548745-[(4-Fluorophenyl)methyl]pyridin-2(1H)-one

生成物 1

HCID 573548755-[(4-fluorophenyl)methyl]-3-nitro-2(1H)-pyridinone

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒2 回

実験手順

A solution of 90% HNO3 (57 mL, 1.22 mol) was added slowly to a stirred solution of 5-[(4-fluorophenyl)methyl]-2(1H)-pyridinone (249 g, 1.22 mol) in TFA (750 mL). The solution was heated at 75° C. for 2 h during which time additional 90% HNO3 (25 mL, 0.5 mol) was added. Water (1L) was added slowly and most of the TFA was removed by distillation. The mixture was allowed to cool to rt and the product was isolated by filtration as a yellow solid: 1H NMR (d6-DMSO) δ 12.76 (1H, br), 8.31 (1H, d, J=2.4 Hz), 7.80 (1H, d, J=2.4 Hz), 7.30 (2H, dd, J=8.6, 5.7 Hz), 7.11 (2H, t, J=8.6 Hz), 3.76 (2H, s); ES+ MS: 249 (M+H+, 100).

後処理

  1. additionwas added
  2. customwas removed by distillation
  3. customthe product was isolated by filtration as a yellow solid

出典と根拠

ORDレコード
ord-91d46795e1df4e1185f1c1181e769bd9
出典データセット
uspto-grants-2014_04
特許番号
US08691991B2

反応ノート

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