Hydrochloric Acid → 1-(2,3-Dihydroxypropyl)-7-(methyloxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1943136Notes

Reaction equation

HRID 1943136 reaction equation
CC(C)(C)C([N:5]([CH2:23][CH:24]1[CH2:28][O:27]C(=O)[O:25]1)[C:6]1[C:11]([CH2:12][CH2:13][C:14](OCCCC)=[O:15])=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=1)=O.Cl>CO>[OH:25][CH:24]([CH2:28][OH:27])[CH2:23][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=2)[CH2:12][CH2:13][C:14]1=[O:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68596362Butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoate

Product 1

HCID 685974381-(2,3-Dihydroxypropyl)-7-(methyloxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-oneYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoate (6.065 g, 13.911 mmol) in methanol (100 ml) was treated with concentrated aqueous HCl (12M, 50 ml) and then heated at reflux for 48 h. The reaction mixture was then concentrated to approximately 50 ml, neutralised with potassium carbonate and extracted with 20% methanol/DCM (3×100 ml). The organic extracts were dried (MgSO4), and evaporated to give the crude product as a yellow oil (2.325 g, 66%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. concentrationThe reaction mixture was then concentrated to approximately 50 ml
  4. extractionextracted with 20% methanol/DCM (3×100 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-2c9c46ade3e14c6a8bd0df1028ab551a
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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