Ammonia → 1,3-dihydro-7-hydroxyamino-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 1729600

Reaction equation

HRID 1729600 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=[O:14])=[CH:12][C:7]=2[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][CH2:4][C:3]1=[O:22].O1CCCC1.O.O.O.C([O-])(=O)C.[Na+].N>C(Cl)Cl.CO>[OH:14][NH:13][C:11]1[CH:10]=[CH:9][C:8]2[N:2]([CH3:1])[C:3](=[O:22])[CH2:4][N:5]=[C:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:12]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 4496NimetazepamHCID 8028TetrahydrofuranHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 123178981,3-dihydro-7-hydroxyamino-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 15 g. (0.05 mol) of 1,3-dihydro-1-methyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 250 ml. of tetrahydrofuran, 250 ml. of methanol, 56 g. of stannous chloride dihydrate and 68 g. of sodium acetate trihydrate was stirred under nitrogen for 3 hours. 1 l. of methylene chloride and 15 ml. of concentrated ammonia was added. The inorganic material was separated by filtration over celite. The filtrate was washed with 1N sodium hydroxide solution, was dried over sodium sulfate and evaporated. Crystallization of the residue from methylene chloride and recrystallization from ethanol/methylene chloride yielded light yellow product with m.p. 211°-213°.

Workup

  1. additionA mixture of 15 g
  2. customThe inorganic material was separated by filtration over celite
  3. washThe filtrate was washed with 1N sodium hydroxide solution
  4. dry with materialwas dried over sodium sulfate
  5. customevaporated
  6. customCrystallization of the residue
  7. customfrom methylene chloride and recrystallization from ethanol/methylene chloride
  8. customyielded light yellow product with m.p. 211°-213°

Sources & evidence

ORD record
ord-5676a85b66054621bb6750b0242c4d8a
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Linked notes

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