Phosphorus oxychloride → 2-Chloro-6,7-dihydro-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one

HRID 1979720Notes

Reaction equation

HRID 1979720 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](=O)[NH:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2.P(Cl)(Cl)([Cl:23])=O>>[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:23])=[N:17][C:18](=[O:19])[N:8]1[CH2:7][CH2:6]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 908572HCID 908572, compound

Product 1

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

Procedure

A mixture of 30.0 g of 9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido(6,1-a)isoquinolin-2,4-dione and 300 ml of phosphorus oxychloride is heated on a steam bath for 4 hours. The excess of phosphorus oxychloride is distilled under reduced pressure. The residue is poured into a cold solution of sodium hydroxide. A yellow solid precipitates which is collected by filtration. The product is purified by passage through a silica gel column using chloroform as eluent. Yield 28.0 g, m.p. 235°-236° C.

Workup

  1. temperatureis heated on a steam bath for 4 hours
  2. distillationThe excess of phosphorus oxychloride is distilled under reduced pressure
  3. additionThe residue is poured into a cold solution of sodium hydroxide
  4. customA yellow solid precipitates which
  5. filtrationis collected by filtration
  6. customThe product is purified by passage through a silica gel column

Sources & evidence

ORD record
ord-08432d9cfeee4853bc714ce97554903c
Source dataset
uspto-grants-1984_11
Patent number
US04482556

Reaction notes

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