Phosphorus oxychloride → 1-Chloro-8-methoxy-4-methyl-5H-pyrido[4,3-b]indole

HRID 1608327Notes

Reaction equation

HRID 1608327 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[C:12]([CH3:17])=[CH:13][NH:14][C:15](=O)[C:6]=3[C:5]=2[CH:4]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:15]1[C:6]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[C:12]([CH3:17])=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13938235HCID 13938235, compound

Product 1

HCID 139382361-Chloro-8-methoxy-4-methyl-5H-pyrido[4,3-b]indole

Procedure

7 g of 1,2-dihydro-8-methoxy-4-methyl-1-oxo-5H-pyrido(4,3-b)indole is heated in 200 ml of phosphorus oxychloride at reflux for 3 days and the excess of oxychloride is evaporated off under reduced pressure. The residue is taken up in 100 ml of boiling water, the mixture is heated to boiling point for 3 minutes and filtered. The filtrate is alkalized cold with ammonia and the precipitate formed is separated, dried, then recrystallized from acetonitrile, giving 5.8 g of yellow micro-crystalls.

Workup

  1. temperatureat reflux for 3 days
  2. customthe excess of oxychloride is evaporated off under reduced pressure
  3. temperaturethe mixture is heated
  4. customfor 3 minutes
  5. filtrationfiltered
  6. customthe precipitate formed
  7. customis separated
  8. customdried
  9. customrecrystallized from acetonitrile
  10. customgiving 5.8 g of yellow micro-crystalls

Sources & evidence

ORD record
ord-2cd022668d7947db80c794d828094cd3
Source dataset
uspto-grants-1989_09
Patent number
US04870180

Reaction notes

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