HCID 12519130, compound → HCID 12519144, compound

HRID 2052702Notes

Reaction equation

HRID 2052702 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[CH2:13][CH2:12]1)(=O)[CH3:2]>O=P(Cl)(Cl)Cl>[ClH:20].[Cl:20][C:16]1[CH:15]=[C:14]2[C:19]3=[C:18]([CH:17]=1)[C:1]([CH3:2])=[N:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]3[CH2:12][CH2:13]2

Participants

3

Reactant 1

HCID 12519130HCID 12519130, compound

Product 1

HCID 12519144HCID 12519144, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A mixture of 286.8 g of 1-(2-acetamidophenyl)-5-chloro-indoline and 1250 ml POCl3 is stirred for 1 hour at room temperature and then slowly heated to reflux. After 20 hours, the resulting solution is permitted to cool and the POCl3 is distilled off at reduced pressure. The residue is then cautiously triturated with absolute ethanol (spontaneous vigorous boiling) and then boiled for 0.5 hour. After cooling to room temperature, the resulting solid is filtered, washed with ethanol and then with ether and dried at 60° C. under vacuum to give 4-chloro-1,2-dihydro-6-methylindolo[1,7-ab][1,5]benzodiazepine hydrochloride, m.p. 251°-254° C. dec.

Workup

  1. temperatureslowly heated to reflux
  2. waitAfter 20 hours
  3. temperatureto cool
  4. distillationthe POCl3 is distilled off at reduced pressure
  5. customThe residue is then cautiously triturated with absolute ethanol (spontaneous vigorous boiling)
  6. waitboiled for 0.5 hour
  7. temperatureAfter cooling to room temperature
  8. filtrationthe resulting solid is filtered
  9. washwashed with ethanol
  10. dry with materialwith ether and dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-55f131a9611242c893d680cc5e96a762
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

Loading…