Hydrazine → 6,7-Dihydro-2-methyl-7-(4-aminobenzoyl)-5H-pyrimido-[5,4-d][1]benzazepine

HRID 1598061Notes

Reaction equation

HRID 1598061 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][N:8]([C:17](=[O:27])[C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1.NN>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][N:8]([C:17](=[O:27])[C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]=2[N:12]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 543797936,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][l]benzazepine

Product 1

HCID 571051316,7-Dihydro-2-methyl-7-(4-aminobenzoyl)-5H-pyrimido-[5,4-d][1]benzazepineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 400 mg of 6,7-dihydro-2-methyl-7-(4-nitrobenzoyl)-5H-pyrimido[5,4-d][1]benzazepine, 87 μl of anhydrous hydrazine and 40 mg of 10% Pd/C in 22 ml of ethyl alcohol is heated at reflux for 1.25 hours, filtered through diatomaceous earth and the pad washed well with methyl alcohol. The combined filtrates are evaporated in vacuo to a residue which is dissolved in ethyl acetate and filtered through a pad of hydrous magnesium silicate and the filtrate concentrated in vacuo to a residue which is dissolved in methyl alcohol and evaporated again to give 330 mg of the desired product as a yellow foam. HR FABMS: Exact mass (M+H): 331.2555.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1.25 hours
  3. filtrationfiltered through diatomaceous earth
  4. washthe pad washed well with methyl alcohol
  5. customThe combined filtrates are evaporated in vacuo to a residue which
  6. dissolutionis dissolved in ethyl acetate
  7. filtrationfiltered through a pad of hydrous magnesium silicate
  8. concentrationthe filtrate concentrated in vacuo to a residue which
  9. dissolutionis dissolved in methyl alcohol
  10. customevaporated again

Sources & evidence

ORD record
ord-100f61163830411681418d5a238e0947
Source dataset
uspto-grants-1998_04
Patent number
US05736538

Reaction notes

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