Sodium Hydroxide → HCID 1793644, compound

HRID 745305Notes

Reaction equation

HRID 745305 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16](Cl)=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2.[OH-:21].[Na+]>C(O)CCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]1=[CH:15][C:16]([O:21][CH2:4][CH2:3][CH2:12][CH3:11])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46787202-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

Product 1

HCID 1793644HCID 1793644, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1.46 g of 9,10-dimethoxy-6,7-dihydro-2-chloro-4H-pyrimido(6,1-a)-isoquinolin-4-one are added to a mixture of 1.0 g of sodium hydroxide and 50.0 ml of n-butanol. The reduction mixture is refluxed for 6 hours. The solent is removed under reduced pressure. The residue is treated with water and extracted with chloroform. The extract is dried over anhydrous Na2SO4 and evaporated to give a white solid. After crystallization from a chloroform-ether mixture, 0.7 g of the title compound is obtained, m.p. 158°-159° C.

Workup

  1. temperatureThe reduction mixture is refluxed for 6 hours
  2. customThe solent is removed under reduced pressure
  3. additionThe residue is treated with water
  4. extractionextracted with chloroform
  5. dry with materialThe extract is dried over anhydrous Na2SO4
  6. customevaporated
  7. customto give a white solid
  8. customAfter crystallization from a chloroform-ether mixture

Sources & evidence

ORD record
ord-24c1a00d3e9a4532bb6641d2982181e6
Source dataset
uspto-grants-1986_07
Patent number
US04598148

Reaction notes

Loading…