Hydrochloric Acid → HCID 12519153, compound

HRID 2052713Notes

Reaction equation

HRID 2052713 reaction equation
[CH2:1]1[N:9]2[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[N:12]=[CH:13][C:7]3=[C:8]2[C:3](=[CH:4][CH:5]=[CH:6]3)[CH2:2]1.[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.[NH4+].[OH-]>O1CCCC1.CCOCC>[C:18]1([CH:13]2[NH:12][C:11]3[CH:14]=[CH:15][CH:16]=[CH:17][C:10]=3[N:9]3[CH2:1][CH2:2][C:3]4=[CH:4][CH:5]=[CH:6][C:7]2=[C:8]34)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 125191331,2-Dihydroindolo[1,7-ab][1,5]benzodiazepineHCID 178418255HCID 178418255, compound

Product 1

HCID 12519153HCID 12519153, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 2.1 g of 1,2-dihydroindolo[1,7-ab][1,5]benzodiazepine in 16 ml of dry tetrahydrofuran is cooled under N2 to 0°-5° C., then treated dropwise with 9.4 ml of a 2.8 molar solution of phenyl magnesium bromide in ether at such a rate as to keep the reaction temperature below 10° C. When the addition is complete, the reaction mixture is refluxed for 3 hours, cooled and then poured into 100 ml ice-water containing 10 ml of concentrated HCl. The resultant mixture is made alkaline with NH4OH and extracted with methylenechloride. The organic phase is separated, washed with brine, dried over Na2SO4 and concentrated to give 6-phenyl-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine, m.p. 161°-164° C.

Workup

  1. temperatureis cooled under N2 to 0°-5° C.
  2. customthe reaction temperature below 10° C
  3. additionWhen the addition
  4. temperaturethe reaction mixture is refluxed for 3 hours
  5. temperaturecooled
  6. extractionextracted with methylenechloride
  7. customThe organic phase is separated
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-bcbed2bcf508401494f35d6c707e9b9c
Source dataset
uspto-grants-1980_01
Patent number
US04186199

Reaction notes

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