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

HRID 2364193노트

반응식

HRID 2364193 반응식
[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

참가 물질

5

반응물 3

HCID 944Nitric Acid2회HCID 962WaterHCID 573548745-[(4-Fluorophenyl)methyl]pyridin-2(1H)-one

생성물 1

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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매2회

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-91d46795e1df4e1185f1c1181e769bd9
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691991B2

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