Water → HCID 11095747, compound

HRID 1082054Notes

Reaction equation

HRID 1082054 reaction equation
Cl[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.O>[Pd].C(O)(=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]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 53771043HCID 53771043, compound

Product 1

HCID 11095747HCID 11095747, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6 g (0.022 mol) of (S)-7-chloro-3-methyl-9-nitro-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione, 200 ml of water, 200 ml of acetic acid and 0.5 g of 5% palladium-on-charcoal are placed in a Parr bottle. The catalytic hydrogenation is carried out under 40 psi at 50° C. The catalyst is filtered, is washed with an acetic acid/water (50/50) mixture and the filtrate is concentrated to dryness. It is taken up in water and the pH adjusted to alkaline with a sodium carbonate solution. The mixture is left stirring for 15 minutes, filtration is carried out, drying is carried out and the solvent evaporated to dryness. 4 g of product are obtained.

Workup

  1. customis carried out under 40 psi at 50° C
  2. filtrationThe catalyst is filtered
  3. washis washed with an acetic acid/water (50/50) mixture
  4. concentrationthe filtrate is concentrated to dryness
  5. waitThe mixture is left
  6. filtrationfiltration
  7. customdrying
  8. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-d080d0b6de6542ed9ae54aaf0fc7a2b8
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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