HCID 53771043, compound → HCID 54406450, compound

HRID 1532452Notes

Reaction equation

HRID 1532452 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[C:5]2[NH:11][C:10](=[O:12])[C@H:9]([CH3:13])[NH:8][C:7](=[O:14])[C:6]=2[CH:15]=1>[Pt].C(O)C>[NH2:16][C:4]1[C:5]2[NH:11][C:10](=[O:12])[C@H:9]([CH3:13])[NH:8][C:7](=[O:14])[C:6]=2[CH:15]=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 1

HCID 53771043HCID 53771043, compound

Product 1

HCID 54406450HCID 54406450, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 298.42 parts of (S)-7-chloro-3,4-dihydro-3-methyl-9-nitro-1H-1,4-benzodiazepine-2,5-dione (prepared as interm. 44) and 3324 parts of ethanol was hydrogenated at 50° C. and normal pressure with 21.04 parts of platinum-on-charcoal catalyst 5%. At the end of the hydrogenation, the temperature was raised to 70° C. The reaction mixture was filtered while hot and the catalyst was washed with boiling ethanol. The filtrate was stirred overnight in an ice-bath and was then concentrated. The residue was cooled on ice. The precipitate was filtered off, washed with methylbenzene and dried in vacuo at 50° C., yielding 187.7 parts (74.6%) of (S)-9-amino-7-chloro-3,4-dihydro-3-methyl-1H-1,4-benzodiazepine-2,5-dione (interm. 77).

Workup

  1. customwas hydrogenated at 50° C.
  2. filtrationThe reaction mixture was filtered while hot and the catalyst
  3. washwas washed with boiling ethanol
  4. concentrationwas then concentrated
  5. temperatureThe residue was cooled on ice
  6. filtrationThe precipitate was filtered off
  7. washwashed with methylbenzene
  8. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-bceea176be724a7581ef6fa9678debe9
Source dataset
uspto-grants-2001_03
Patent number
US06201119B1

Reaction notes

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