Phosphorus oxychloride → 1,2-Dihydroindolo[1,7-ab][1,5]benzodiazepine hydrochloride

HRID 2052700Notes

Reaction equation

HRID 2052700 reaction equation
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11]1)=O.P(Cl)(Cl)([Cl:21])=O>>[ClH:21].[CH2:11]1[N:10]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[CH:1][C:17]3=[C:18]2[C:13](=[CH:14][CH:15]=[CH:16]3)[CH2:12]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12519124N-[2-(2,3-Dihydro-1H-indol-1-yl)phenyl]formamide

Product 1

HCID 125191341,2-Dihydroindolo[1,7-ab][1,5]benzodiazepine hydrochloride

Procedure

A mixture of 14.0 g of 1-(2-formamidophenyl)indoline and 50 ml of fresh phosphorus oxychloride are stirred and heated under N2. The mixture is refluxed 4.0 hours, then left at room temperature 18 hours. Excess POCl3 is then removed, leaving a solid which is triturated and boiled with absolute ethanol. The mixture is stirred 1 hour to homogenize the fine solid, then filtered, washed with ethanol, and dried to afford 1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine hydrochloride, m.p. 228°-230° C. dec.

Workup

  1. temperatureheated under N2
  2. temperatureThe mixture is refluxed 4.0 hours
  3. customExcess POCl3 is then removed
  4. customleaving a solid which
  5. customis triturated
  6. stirringThe mixture is stirred 1 hour
  7. stirringto homogenize the fine solid
  8. filtrationfiltered
  9. washwashed with ethanol
  10. customdried

Sources & evidence

ORD record
ord-046567728a214618b26597b57d28de06
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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