Methanol → Methyl 3-(6-aminopyridin-3-yl)butanoate

HRID 49715Notes

Reaction equation

HRID 49715 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([CH3:14])[CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:20]O>>[NH2:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([CH3:14])[CH2:10][C:11]([O:13][CH3:20])=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 69687733(RS) 3-(6-amino-pyrid-3-yl)-butanoic acid hydrochloride

Product 1

HCID 17946640Methyl 3-(6-aminopyridin-3-yl)butanoate

Procedure

A solution of (RS) 3-(6-amino-pyrid-3-yl)-butanoic acid hydrochloride (12.0 g, Reference Example 20) in methanol (300 mL) was treated with concentrated sulphuric acid (3.0 mL) then heated at reflux temperature for 8 hours. The reaction mixture was concentrated, then basefied with 5% aqueous sodium bicarbonate and then extracted with ethyl acetate . The extracts were washed with water, then with brine, then dried over magnesium sulphate and then evaporated to give the title compound (7.6 g) as a yellow oil.

Workup

  1. temperaturethen heated
  2. temperatureat reflux temperature for 8 hours
  3. concentrationThe reaction mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water
  6. dry with materialwith brine, then dried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-85091cf6242f41f795cf2668558cdfb4
Source dataset
uspto-grants-2004_03
Patent number
US06706738B2

Reaction notes

Loading…