Ethanol → 6-(4-(2-Chloroethyl)phenyl)-pyridin-2-ylamine hydrochloride

HRID 991937Notes

Reaction equation

HRID 991937 reaction equation
CC1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][Cl:22])=[CH:16][CH:15]=3)[N:9]=2)C(C)=CC=1.C(O)C.Cl.NO>O>[ClH:22].[Cl:22][CH2:21][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:10]2[N:9]=[C:8]([NH2:3])[CH:13]=[CH:12][CH:11]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 158961902-[4-(2-chloroethyl)phenyl]-6-(2,5-dimethyl-1H-pyrrol-1-yl)Pyridine

Product 1

HCID 184144446-(4-(2-Chloroethyl)phenyl)-pyridin-2-ylamine hydrochlorideYield 199.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet were added 9.0 g (29.0 mmol) 2-(2, 5-dimethylpyrrol-1-yl)-6-(4-(2-chloroethyl)phenyl)-pyridine, 250 mL ethanol, 50 mL water, and 10.1 g (145 mmol) hydroxylamine hydrochloride. The reaction was refluxed for 36 hours, cooled, and the solvent was evaporated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate, and evaporated. The residue was chromatographed on silica gel using 2% methanol in methylene chloride as eluant to afford 7.8 g (88%) of the product as a light brown solid.

Workup

  1. customTo a 500 mL round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperatureThe reaction was refluxed for 36 hours
  3. temperaturecooled
  4. customthe solvent was evaporated
  5. washwashed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was chromatographed on silica gel using 2% methanol in methylene chloride as eluant

Sources & evidence

ORD record
ord-6ac9f0ef17e6448abe17c646e2d3afe7
Source dataset
uspto-grants-2002_10
Patent number
US06465491B2

Reaction notes

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