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

HRID 468782Notes

Reaction equation

HRID 468782 reaction equation
[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

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 86674943tert-butyl N-[6-chloro-4-(1-hydroxyethyl)-3-pyridyl]carbamate

Product 1

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

Procedure

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.

Workup

  1. customevaporated in vacuo
  2. dissolutionThe resulting residue was dissolved in dichloromethane
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-dd82061ae42b44deb0f2dc7ed7ceb987
Source dataset
uspto-grants-2014_01
Patent number
US08623889B2

Reaction notes

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