Methanol → 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime

HRID 2383829

Reaction equation

HRID 2383829 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH:4]=O.Cl.[NH2:24][OH:25].N1C=CC=CC=1.CO>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][N:12]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][C:20]=3[CH3:21])[C:11]2=[O:22])=[CH:6][C:3]=1[CH:4]=[N:24][OH:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866493982-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde

Product 1

HCID 866493992-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oximeYield 70.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde (I-113a: 230 mg, 0.769 mmol), hydroxylamine hydrochloride (160 mg, 2.307 mmol) and pyridine (5 mL) were taken in a reaction flask and the flask was stirred at room temperature for 18 hours under nitrogen atmosphere. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The organic layer was dried over Na2SO4 and concentrated. The concentrate was washed with diethyl ether and decanted to afford 170 mg of 2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzaldehyde oxime (70.8% yield).

Workup

  1. customThe reaction mixture was partitioned between ice water and ethylacetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. washThe concentrate was washed with diethyl ether
  5. customdecanted

Sources & evidence

ORD record
ord-c996af0dc9fb4a10be0abfeec5b082cd
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Linked notes

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