Methanol → 1-[3-Fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80141Notes

Reaction equation

HRID 80141 reaction equation
[OH-:1].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[C:13]2=[O:24])=[CH:8][C:7]=1[F:25])(=O)[CH3:4].Cl.[NH2:27]O.CO>O.C(O)C.C(Cl)(Cl)Cl>[F:25][C:7]1[CH:8]=[C:9]([N:12]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[CH3:23])[C:13]2=[O:24])[CH:10]=[CH:11][C:6]=1[C:3](=[N:27][OH:1])[CH3:4]

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 687845161-(4-Acetyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Product 1

HCID 866493971-[3-Fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneYield 87.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

NaOH (72.7 mg, 1.8193 mmol) in water (5 mL) was added dropwise to a stirred solution of 1-(4-acetyl-3-fluoro-phenyl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-111a: 380 mg, 1.2128 mmol) and hydroxylamine hydrochloride in ethanol (10 mL) over a period of 5 minutes. The resulting mixture was stirred at room temperature for 4 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). Ice was added to the reaction mixture to yield a precipitate which was collected and dried under reduced pressure to afford 350 mg of 1-[3-Fluoro-4-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-111b: 87.9% yield).

Workup

  1. additionIce was added to the reaction mixture
  2. customto yield a precipitate which
  3. customwas collected
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-26b36e1809d54b53a83c6612083d264f
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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