Pyridine → HCID 86679082, compound

HRID 1039357Notes

Reaction equation

HRID 1039357 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](=O)[CH2:11][F:12])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl.[CH3:21][O:22][NH2:23]>CO.Cl>[CH3:21][O:22][N:23]=[C:10]([CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:11][F:12]

Participants

6

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 86679081HCID 86679081, compound

Product 1

HCID 86679082HCID 86679082, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred suspension of 4-(4-chloro-phenyl)-1-fluoro-butan-2-one (0.13 g; 0.62 mmol) in methanol (1.3 ml) was added pyridine (80 μl; 0.99 mmol) followed by a portion wise addition of methoxyamine hydrochloride (78 mg; 0.93 mmol). The reaction mixture was stirred for 16 h at 23° C. The mixture was poured in 1 N hydrochloric acid (5 ml), extracted with dichloromethane (3×3 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford 0.13 g (94% of theory) of 4-(4-chloro-phenyl)-1-fluoro-butan-2-one O-methyl-oxime (mixture of E/Z-isomers) as a yellow oil.

Workup

  1. extractionextracted with dichloromethane (3×3 ml)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-48a26986342044b4a5796e48dacf752c
Source dataset
uspto-grants-2013_10
Patent number
US08552049B2

Reaction notes

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