Hydrazine hydrate (1:1) → HCID 21701439, compound

HRID 1596347Notes

Reaction equation

HRID 1596347 reaction equation
C1(=O)[N:5]([CH:6]2[N:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:10]3[CH:20]=[CH:21][CH:22]=[C:23]([CH2:24][CH3:25])[C:9]=3[NH:8][C:7]2=[O:26])C(=O)C2=CC=CC=C12.O.NN>CO.O1CCCC1.C(OCC)(=O)C>[NH2:5][CH:6]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])[C:10]2[CH:20]=[CH:21][CH:22]=[C:23]([CH2:24][CH3:25])[C:9]=2[NH:8][C:7]1=[O:26]

Participants

6

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21701454HCID 21701454, compound

Product 1

HCID 21701439HCID 21701439, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3RS)-3-phthalimido-9-ethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (6.0 g) and hydrazine hydrate (1.05 g) in a mixture of methanol and tetrahydrofuran (1:1, 60 ml) was refluxed with stirring for 3 hours. The reaction mixture was allowed to cool to room temperature, and the resultant precipitates were filtered off. The filtrate and the washings were combined and evaporated in vacuo to give a residue, which was dissolved in ethyl acetate and washed with a saturated aqueous solution of sodium bicarbonate, water and brine successively. The solvent was dried over sodium sulfate and evaporated in vacuo to afford a pale yellow powder, which was washed with diisopropyl ether and collected by filtration to give (3RS)-3-amino-9-ethyl-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepin-2-one (3.37 g, 81.0%).

Workup

  1. temperaturewas refluxed
  2. customthe resultant precipitates
  3. filtrationwere filtered off
  4. customevaporated in vacuo
  5. customto give a residue, which
  6. washwashed with a saturated aqueous solution of sodium bicarbonate, water and brine successively
  7. dry with materialThe solvent was dried over sodium sulfate
  8. customevaporated in vacuo
  9. customto afford a pale yellow powder, which
  10. washwas washed with diisopropyl ether
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-9cc81d8ab95c472c98c804591ffaeb16
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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