Hydrazine hydrate (1:1) → 1,4,5,6-Tetrahydro-6-(4-nitrobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepine

HRID 1733978Notes

Reaction equation

HRID 1733978 reaction equation
C[N:2]([CH:4]=[C:5]1[CH2:11][CH2:10][N:9]([C:12](=[O:22])[C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[C:8]2[N:23]=[CH:24][CH:25]=[CH:26][C:7]=2[C:6]1=O)C.O.[NH2:29]N>CO>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]([N:9]2[CH2:10][CH2:11][C:5]3[CH:4]=[N:2][NH:29][C:6]=3[C:7]3[CH:26]=[CH:25][CH:24]=[N:23][C:8]2=3)=[O:22])=[CH:14][CH:15]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 53844267HCID 53844267, compound

Product 1

HCID 544497301,4,5,6-Tetrahydro-6-(4-nitrobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepineYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slurry of 0.51 g of 6-[(dimethylamino)methylene]-6,7,8,9-tetrahydro-9-(4-nitrobenzoyl)-5H-pyrido[2,3-b]azepin-5-one in 17 ml of methanol under argon is added 0.14 g of hydrazine hydrate. The mixture is stirred overnight and the solvent removed under vacuum. The residue is dissolved in hot chloroform-methanol (95:5) and filtered through silica gel and washed filter pad with chloroform-methanol (95: 5). The filtrate is concentrated to dryness to give 0.48 g of yellow solid.

Workup

  1. customthe solvent removed under vacuum
  2. dissolutionThe residue is dissolved in hot chloroform-methanol (95:5)
  3. filtrationfiltered through silica gel
  4. washwashed
  5. filtrationfilter pad with chloroform-methanol (95: 5)
  6. concentrationThe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-5df1a56eb94147b8ad032c12a30f61d7
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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