Ammonia → 2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-(hydroxyamino)-5-phenyl-

HRID 1729599

Reaction equation

HRID 1729599 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1)([O-])=[O:2].O.O.O.C([O-])(=O)C.[Na+].N>O1CCCC1.CO>[OH:2][NH:1][C:4]1[CH:5]=[CH:6][C:7]2[NH:13][C:12](=[O:14])[CH2:11][N:10]=[C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]=2[CH:21]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 4506NitrazepamHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 123178972H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-(hydroxyamino)-5-phenyl-

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 16.8 g. of 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 500 ml. of tetrahydrofuran, 250 ml. of methanol, 56 g. of stannous chloride dihydrate and 68 g. of sodium acetate trihydrate was stirred at room temperature under an atmosphere of nitrogen for 24 hours. 1 l. of tetrahydrofuran and 15 ml. of concentrated ammonia were then added. The inorganic salts were removed by filtration through celite. The filtrate was evaporated. The solid residue was stirred with 100 ml. of methylene chloride and 250 ml. of water for 20 minutes under nitrogen. The insoluble crystals were collected to leave light yellow material. For analysis it was recrystallized from ethanol/methylene chloride, m.p. 186°-187°.

Workup

  1. additionA mixture of 16.8 g
  2. customThe inorganic salts were removed by filtration through celite
  3. customThe filtrate was evaporated
  4. customThe insoluble crystals were collected
  5. customto leave light yellow material
  6. customFor analysis it was recrystallized from ethanol/methylene chloride, m.p. 186°-187°

Sources & evidence

ORD record
ord-0dea0421232045f39b51c21597ee4833
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Linked notes

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