Hydrochloric Acid → Gyki 52895

HRID 1762795Notes

Reaction equation

HRID 1762795 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+].[H][H]>O.N1C=CC=CC=1>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 35384-(8-Methyl-9H-1,3-dioxolo(4,5-H)(2,3)benzodiazepin-5-yl)benzenamineHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 3539Gyki 52895

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

A mixture of 8.80 g (0.03 moles) of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine, 5.675 g (0.15 moles) of sodium borohydride and 80 ml of pyridine is stirred on a water bath heated to boiling, for 5 hours. When the reaction mixture is cool, 90 ml of water is added to it, then, under ice-cooling, 260 ml of an aqueous hydrochloric acid solution containing 110 ml of concentrated hydrochloric acid are added, and thereafter 115 ml of 40% aqueous sodium hydroxide solution are dropped to the reaction mixture. On adding the water, hydrogen evolution occurs, on adding the base the aimed compound separates in the form of an oil containing pyridine. The mixture is then extracted with benzene, the benzene phase is shaken with water, dried, clarified with activated charcoal and evaporated under reduced pressure. The residue is taken up in 50 ml of water, the crude product is filtered off, washed 5 times with 10 ml of water, dried at 50°-60° C., recrystallized from 16 ml of 50% aqueous ethanol and finally the crystal water is removed at 100°-105° C. under reduced pressure.

Workup

  1. temperatureheated
  2. temperatureWhen the reaction mixture is cool
  3. temperatureunder ice-cooling
  4. additionare added

Sources & evidence

ORD record
ord-9b09dd63e9f04e50a7890b4c84af922c
Source dataset
uspto-grants-1989_05
Patent number
US04835152

Reaction notes

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