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

HRID 1729601Notes

Reaction equation

HRID 1729601 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:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:22])[C:11](=[O:23])[CH2:10][N:9]=1.O1CCCC1.O.O.O.C([O-])(=O)C.[Na+].N>CO>[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]([NH:19][OH:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:22])[C:11](=[O:23])[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3380FlunitrazepamHCID 8028TetrahydrofuranHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 1487602H-1,4-Benzodiazepin-2-one, 5-(2-fluorophenyl)-1,3-dihydro-7-(hydroxyamino)-1-methyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 16 g. (0.05 mol) of 1,3-dihydro-5-(2-fluorophenyl)-1-methyl-7-nitro-2H-1,4-benzodiazepin-2-one, 500 ml. of tetrahydrofuran, 250 ml. of methanol, 68 g. of sodium acetate trihydrate and 56 g. of stannous chloride dihydrate was stirred under nitrogen for 6 hours. 25 ml. of concentrated ammonia was added and the inorganic salts were removed by filtration through celite. The filtrate was washed well with 2 l. of tetrahydrofuran. The filtrate was evaporated and the solid residue was dissolved in ethanol/tetrahydrofuran. The solution was again filtered with celite and concentrated. The separated crystals were collected to leave light yellow product. For analysis it was recrystallized from ethanol/tetrahydrofuran, m.p. 228°-230° dec.

Workup

  1. additionA mixture of 16 g
  2. customthe inorganic salts were removed by filtration through celite
  3. washThe filtrate was washed well with 2 l
  4. customThe filtrate was evaporated
  5. dissolutionthe solid residue was dissolved in ethanol/tetrahydrofuran
  6. filtrationThe solution was again filtered with celite and
  7. concentrationconcentrated
  8. customThe separated crystals were collected
  9. customto leave light yellow product
  10. customFor analysis it was recrystallized from ethanol/tetrahydrofuran, m.p. 228°-230° dec.

Sources & evidence

ORD record
ord-c19b7c4e77874a139a5e237a7526e80b
Source dataset
uspto-grants-1976_11
Patent number
US03989681

Reaction notes

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