Ethanol → HCID 23155298, compound

HRID 1912886Notes

Reaction equation

HRID 1912886 reaction equation
C(O)C.CC1[N:6]([C:11]2[CH:23]=[CH:22][C:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)=[C:13]([C:24]([F:27])([F:26])[F:25])[CH:12]=2)C(C)=CC=1.Cl.NO>C(N(CC)CC)C>[N:19]1[CH:20]=[CH:21][C:16]([CH2:15][C:14]2[CH:22]=[CH:23][C:11]([NH2:6])=[CH:12][C:13]=2[C:24]([F:25])([F:26])[F:27])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 23155230HCID 23155230, compound

Product 1

HCID 23155298HCID 23155298, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 10 mL of an ethanol solution of 227 mg (0.69 mmol) of 4-[4-(2,5-dimethyl-pyrrol-1-yl)-2-trifluoromethyl-benzyl]-pyridine, 191 mg (2.75 mmol) of hydroxylamine hydrochloride and 200 μL of triethylamine were added and the mixture solution was refluxed with stirring for 18 hours. The reaction solution was partitioned between a saturated sodium bicarbonate solution and ethyl acetate and the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=1:1) to obtain 144 mg (83%) of a target product as a pale yellow oil.

Workup

  1. temperaturethe mixture solution was refluxed
  2. customThe reaction solution was partitioned between a saturated sodium bicarbonate solution and ethyl acetate
  3. washthe organic layer was washed with a saturated sodium chloride solution
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by a silica gel column (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-aeb3eb684d4a4f34b9bd2232bed58c5a
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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