Hydrazine → 2,4,5,6-Tetrahydro-2-methyl-6-(4-aminobenzoyl)-pyrazolo[4,3-d][1]benzazepine

HRID 1938247Notes

Reaction equation

HRID 1938247 reaction equation
[CH3:1][N:2]1[CH:26]=[C:5]2[CH2:6][CH2:7][N:8]([C:15](=[O:25])[C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1.NN>C(O)C.[Pd]>[CH3:1][N:2]1[CH:26]=[C:5]2[CH2:6][CH2:7][N:8]([C:15](=[O:25])[C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 571133932,4,5,6-Tetrahydro-2-methyl-6-(4-nitrobenzoyl)-pyrazolo[4,3-d][1]benzazepin

Product 1

HCID 538901292,4,5,6-Tetrahydro-2-methyl-6-(4-aminobenzoyl)-pyrazolo[4,3-d][1]benzazepineYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 0.520 g of 2,4,5,6-tetrahydro-2-methyl-6-(4-nitrobenzoyl)pyrazolo[4,3-d][1]benzazepine, 118 μl of anhydrous hydrazine and 52 mg of 10% palladium-on-carbon in 30 ml of absolute ethyl alcohol is heated at reflux for 1 hour. The reaction mixture is filtered through diatomaceous earth and the cake washed with 100 ml of methyl alcohol and 1:1 chloroform-methyl alcohol to give 430 mg of the desired product as off-white crystals. CIMS(CH4)MH+ =319.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe reaction mixture is filtered through diatomaceous earth
  4. washthe cake washed with 100 ml of methyl alcohol and 1:1 chloroform-methyl alcohol

Sources & evidence

ORD record
ord-a018fc119a724d8d99f3cb18e42bf001
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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