Sodium Hydroxide → 8-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

HRID 1758781Notes

Reaction equation

HRID 1758781 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[N:12]2[C:22]([CH3:25])=[N:23][N:24]=[C:11]2[C:10]([CH3:27])([CH3:26])[N:9]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]3[C:22]([CH3:25])=[N:23][N:24]=[C:11]3[C:10]([CH3:27])([CH3:26])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24287Tin tetrachlorideHCID 205085396-(o-fluorophenyl)-1,4,4-trimethyl-8-nitro-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Product 1

HCID 205085588-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

43.6 g (0.12 mol) of 6-(o-fluorophenyl)-1,4,4-trimethyl-8-nitro-4H-s-triazolo[4,3-a][1,4]benzodiazepine in 600 ml of concentrated hydrochloric acid are treated portionwise with a total of 80.55 g (0.36 mol) of tin chloride in such a manner that the temperature of the mixture does not exceed 85° C. Subsequently, the mixture is stirred at room temperature for 1 hour, cooled to 0° C. and cautiously neutralised with 900 ml of 10 N sodium hydroxide. After extracting the remaining suspension three times with methylene chloride, the combined organic phases are washed with saturated sodium chloride solution, dried and evaporated. Recrystallisation of the residue from 350 ml of ethanol at -30° C. gives 8-amino-6-(o-fluorophenyl)-1,4,4-trimethyl-4H-s-triazolo[4,3-a][1,4]benzodiazepine of melting point 294° C.

Workup

  1. customdoes not exceed 85° C
  2. temperaturecooled to 0° C.
  3. extractionAfter extracting the remaining suspension three times with methylene chloride
  4. washthe combined organic phases are washed with saturated sodium chloride solution
  5. customdried
  6. customevaporated
  7. customRecrystallisation of the residue from 350 ml of ethanol at -30° C.

Sources & evidence

ORD record
ord-c8980772c9734e4c859d797f6929f8bd
Source dataset
uspto-grants-1983_02
Patent number
US04374773

Reaction notes

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