Hydrogen Peroxide → HCID 9795327, compound

HRID 723819Notes

Reaction equation

HRID 723819 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[OH:18]O>C(O)(=O)C>[CH:14]1[C:9]([NH:8][C:6]([C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[N+:3]([O-:18])[CH:4]=2)=[O:7])=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=1

Participants

4

Reactant 2

HCID 784Hydrogen Peroxide2×HCID 2653166HCID 2653166, compound

Product 1

HCID 9795327HCID 9795327, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-chloro-N-(4-fluoro-phenyl)-nicotinamide (2.06 g, 8.2 mmole) in 30 mL of acetic acid was added 30 mL of aqueous hydrogen peroxide (30%). The mixture was warmed to 70° C. and stirred for 18 hours, and then 20 mL of additional hydrogen peroxide (30%) was added and stirred for 2 hours. The mixture was then cooled, concentrated in vacuo and diluted with water (100 mL). Isolation of the precipitate by vacuum filtration afforded 0.43 g (20%) of the desired product as a white solid: 1H NMR (300 MHz, DMSO-d6) δ7.19 (m 2H), 7.75 (M, 3H), 7.95 (M, 1H), 8.94 (d, 1H, J=2.2 Hz), 10.5 (s, 1H); MS (EI) m/z 267.19 (M+H)+.

Workup

  1. stirringstirred for 2 hours
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated in vacuo
  4. additiondiluted with water (100 mL)
  5. filtrationIsolation of the precipitate by vacuum filtration

Sources & evidence

ORD record
ord-ce317864110e40169b341f79670707fb
Source dataset
uspto-grants-2006_11
Patent number
US07141590B2

Reaction notes

Loading…