Nitric Acid → 5-[(4-Fluorophenyl)methyl]-3-nitropyridin-2(1H)-one

HRID 2364193Notes

Reaction equation

HRID 2364193 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 573548755-[(4-Fluorophenyl)methyl]-3-nitropyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-91d46795e1df4e1185f1c1181e769bd9
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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