Water → 5-(4-Fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrole-3-carboxaldehyde O-methyloxime

HRID 1244984Notes

Reaction equation

HRID 1244984 reaction equation
Cl.[CH3:2][O:3][NH2:4].C(N(CC)CC)C.[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[NH:20][CH:21]=[C:22]([CH:30]=O)[C:23]=2[C:24]2[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=2)=[CH:15][CH:14]=1.O>CO>[CH3:2][O:3][N:4]=[CH:30][C:22]1[C:23]([C:24]2[CH:25]=[CH:26][N:27]=[CH:28][CH:29]=2)=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[NH:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 219226862-(4-Fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrrole

Product 1

HCID 1363804435-(4-Fluorophenyl)-4-(pyridin-4-yl)-1H-pyrrole-3-carboxaldehyde O-methyloximeYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.83 g (9.58 mmol) of O-methylhydroxylamine hydrochloride and 1.56 ml (11.2 mmol) of triethylamine were added to a solution of 0.85 mg (3.2 mmol) of 2-(4-fluorophenyl)-4-formyl-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in Example 1(iii) above] in 17 ml of methanol. The resulting mixture was heated under reflux for 30 minutes, after which water was added to the reaction mixture which was then extracted with ethyl acetate. The organic extract was washed with water and concentrated by evaporation under reduced pressure. The resulting residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 728 mg (yield 77%) of the title compound as a pale yellow powder.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. extractionwas then extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe resulting residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-8239d5911c9b4560842089be313c5807
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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