Dichloromethane → 1-(5-Amino-2-chloropyridin-4-yl)ethanol

反応式

[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8]C(=O)OC(C)(C)C)=[C:4]([CH:16]([OH:18])[CH3:17])[CH:3]=1.C(Cl)Cl.FC(F)(F)C(O)=O>>[NH2:8][C:5]1[C:4]([CH:16]([OH:18])[CH3:17])=[CH:3][C:2]([Cl:1])=[N:7][CH:6]=1

参加物

反応物 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 86674943tert-butyl N-[6-chloro-4-(1-hydroxyethyl)-3-pyridyl]carbamate

生成物 1

HCID 866749441-(5-Amino-2-chloropyridin-4-yl)ethanol収率 87.3%

実験手順

To a solution of tert-butyl 6-chloro-4-(1-hydroxyethyl)pyridin-3-ylcarbamate (823 mg, 3.02 mmol) in methylene chloride (40 mL, 500 mmol) was added trifluoroacetic acid (2 mL, 20 mmol). The reaction mixture was stirred at room temperature for 5 hours and then evaporated in vacuo. The resulting residue was dissolved in dichloromethane and washed with saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and evaporated in vacuo to yield 455.2 mg (87%) of 1-(5-amino-2-chloropyridin-4-yl)ethanol which was carried forward without purification.