Sodium Hydroxide → HCID 20542102, compound

HRID 2286161Notes

Reaction equation

HRID 2286161 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[NH:12][C:11](=[O:22])[CH:10]([CH3:23])[N:9]=1.[Sn](Cl)(Cl)(Cl)Cl.[OH-].[Na+]>Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[NH:12][C:11](=[O:22])[CH:10]([CH3:23])[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 20542078(+)-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 20542102HCID 20542102, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

62.7 g (0.2 mol) of crude rac-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-7-nitro-2H-1,4-benzodiazepin-2-one in 1 l of concentrated hydrochloric acid is treated portionwise while stirring with a total of 135.5 g (0.6 mol) of tin chloride, stirred at room temperature for 2 hours and the mixture is neutralised in the cold with 10 N sodium hydroxide. The aqueous phase is extracted with a total of 8 l of methylene chloride/ethanol (4:1), the combined organic extracts are washed with saturated sodium chloride solution, dried and evaporated. From ether there is obtained 7-amino-5-(o-fluorophenyl)-1,3-dihydro-3-methyl-2H-1,4-benzodiazepin-2-one of melting point 270°.

Workup

  1. extractionThe aqueous phase is extracted with a total of 8 l of methylene chloride/ethanol (4:1)
  2. washthe combined organic extracts are washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b828b125fe21415cbb52a075abc9ad75
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

Loading…