Hydrochloric Acid → 1-(4-Fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acid

HRID 2117172Notes

Reaction equation

HRID 2117172 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([C:17]([O:19]C)=[O:18])[C:9]2=[O:21])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([C:17]([OH:19])=[O:18])[C:9]2=[O:21])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21081724Methyl 1-(4-fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylate

Product 1

HCID 210815281-(4-Fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylic acidYield 66%

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 1-(4-fluorophenyl)-5-nitro-2-oxo-1,2-dihydropyridine-3-carboxylate (75 mg, 0.245 mmol) and 2 N NaOH solution (1 mL) was stirred at 80° C. for 2 h. The reaction mixture was cooled to rt and acidified with 1 N HCl solution. The solid that formed was collected, washed with water and dried to afford the title compound (45 mg, 66%), which was used directly in the next reaction. 1H NMR (DMSO-d6) δ 13.41 (s, 1H), 9.28 (d, 1H, J=3.2 Hz), 8.70 (d, 1H, J=3.2 Hz), 7.60 (m, 2H), 7.41 (m, 2H); MS(ESI+) m/z 279 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customThe solid that formed
  3. customwas collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-808feef12a3e4169942978d9636adc56
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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