Ammonium Acetate → HCID 69515670, compound

HRID 458436Notes

Reaction equation

HRID 458436 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([CH2:12][N+:13]([O-:15])=[O:14])=O.C([O-])(=O)C.[NH4+:20]>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9]/[C:10](/[NH2:20])=[CH:12]/[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 18441887HCID 18441887, compound

Product 1

HCID 69515670HCID 69515670, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The mixture of 1-(2,4-difluorophenyl)-3-nitroacetone (9.4 g, 43.7 mmol) and ammonium acetate (16.8 g, 219 mmol) in 250 ml benzene was refluxed with Dean-Stark setup for 5 hours. The reaction mixture was then partitioned between ether and water. The organic portion was washed with brine and dried over sodium sulfate. Removing the solvent afforded 8.5 g light brown solid. 1H-NMR (400 MHz, CD3OD) δ 7.20 (m, 1H), 6.84 (m, 3H), 3.65 (s, 2H) ppm. ESI-MS m/z 215 (M+H)+.

Workup

  1. temperaturewas refluxed with Dean-Stark setup for 5 hours
  2. customThe reaction mixture was then partitioned between ether and water
  3. washThe organic portion was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoving the solvent
  6. customafforded 8.5 g light brown solid

Sources & evidence

ORD record
ord-0d957aea413d4c22ab438b9d591f2f9d
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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