Sodium Bicarbonate → 1,4,5,6-Tetrahydro-6-(4-aminobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepine

HRID 1733979Notes

Reaction equation

HRID 1733979 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[N:18][NH:19][C:13]=3[C:12]3[CH:20]=[CH:21][CH:22]=[N:23][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-])=O.C([O-])(O)=O.[Na+]>C(O)C>[NH2:1][C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]2[CH2:16][CH2:15][C:14]3[CH:17]=[N:18][NH:19][C:13]=3[C:12]3[CH:20]=[CH:21][CH:22]=[N:23][C:11]2=3)=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 544497301,4,5,6-Tetrahydro-6-(4-nitrobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepine

Product 1

HCID 194387381,4,5,6-Tetrahydro-6-(4-aminobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepineYield 64.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 0.170 g of 1,4,5,6-tetrahydro-6-(4-nitrobenzoyl)pyrazolo[3,4-d]pyrido[2,3-b]azepine in 8 ml of ethanol under argon is added 0.573 g of stannous chloride dihydrate (SnCl2.2H2O). The mixture is refluxed for 1 hour, diluted with ice-water and made basic with 10% NaHCO3 solution. The mixture is stirred 3.5 hours and extracted with chloroform (3 times). The extract is dried (MgSO4) and the solvent removed under vacuum. Chromatography on silica gel with ethyl acetate as eluent gives 0.10 g of off-white crystals.

Workup

  1. temperatureThe mixture is refluxed for 1 hour
  2. extractionextracted with chloroform (3 times)
  3. dry with materialThe extract is dried (MgSO4)
  4. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-76b104c714cb442dbf5ecf59627dbe14
Source dataset
uspto-grants-1996_07
Patent number
US05532235

Reaction notes

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