Hydroxylamine → (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime

HRID 867531Notes

Reaction equation

HRID 867531 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[NH2:22][OH:23]>C(O)C>[Cl:1][C:2]1[C:7]2[C:8](=[O:21])[N:9]3[CH2:20][CH2:19][CH2:18][C@H:10]3[C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:22][OH:23])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 54287641(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile

Product 1

HCID 53703069(S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.0 g (23.4 mmol) of (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carbonitrile are stirred at boiling temperature for 1.5 hours together with about 1.0 g of freshly prepared hydroxylamine in 90 ml of ethanol. By cooling, filtering off the precipitated material, washing with ether and drying there is obtained (S)-8-chloro-11,12,13,13a-tetrahydro-9-oxo-9H-imidazo[1,5-a]pyrrolo[2,1-c][1,4]benzodiazepine-1-carboxamidoxime of melting point 249°-250°. By chromatography of the residue from the mother liquor on silica gel and subsequent crystallization from ethyl acetate there is obtained a second portion of the desired amidoxime.

Workup

  1. customfor 1.5 hours
  2. temperatureBy cooling
  3. filtrationfiltering off the precipitated material
  4. washwashing with ether
  5. customdrying there

Sources & evidence

ORD record
ord-e36f1d1892084c639e94e7c85e3c8488
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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