Acetic Acid → 1,3-Dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one

HRID 2058603Notes

Reaction equation

HRID 2058603 reaction equation
C1([O:7][C:8]([C:10]2[N:14]([CH3:15])[N:13]=[C:12]([CH3:16])[C:11]=2[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)=O)C=CC=CC=1.C(O)(=O)C>C1(C)C=CC=CC=1.[Pd]>[CH3:15][N:14]1[C:10]2[C:8](=[O:7])[NH:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:11]=2[C:12]([CH3:16])=[N:13]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 53961222HCID 53961222, compound

Product 1

HCID 205498761,3-Dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-oneYield 70.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

2.4 g of 1,3-dimethyl-4-[(2-nitrophenyl)amino]pyrazole-5-carboxylic acid phenyl ester are hydrogenated in 150 ml of toluene and 5 ml of glacial acetic acid using 0.75 g of 10% strength palladium-on-charcoal at room temperature for 2.1 hours in a circulatory hydrogenation apparatus. The solution is filtered and concentrated in vacuo; the residue is chromatographed over a silica gel column using 1:1 petroleum ether (50°/70° C.)/ethyl acetate to yield 1.1 g of 1,3-dimethyl-1,4,9,10-tetrahydropyrazolo[4,3-b][1,5]benzodiazepin-10-one, mp 189° to 190° C.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue is chromatographed over a silica gel column
  4. custom1:1 petroleum ether (50°/70° C.)/ethyl acetate

Sources & evidence

ORD record
ord-924f1c562a694d90884eab7fa8e6f493
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

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