Hydrochloric Acid → Thieno[2,3-b]pyridine-2,3-diamine HCl salt

HRID 1615666Notes

Reaction equation

HRID 1615666 reaction equation
[N+:1]([C:4]1[S:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]=1[NH2:13])([O-])=O.[ClH:14].CCOC(C)=O>CCO.[Ni]>[ClH:14].[S:12]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[C:5]([NH2:13])=[C:4]1[NH2:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 131693742-Nitrothieno[2,3-b]pyridin-3-amine

Product 1

HCID 68089372Thieno[2,3-b]pyridine-2,3-diamine HCl salt

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-nitrothieno[2,3-b]pyridin-3-amine (1.1 g, 5.6 mmol) in EtOH (60 mL) was added Raney Ni (1 g), followed by slow addition of N2H4.H2O (1.4 g, 22 mmol). The mixture was stirred at room temperature for 2 h. A solution of HCl in EtOAc (1 M, 18 mL, 18 mmol) was added to the reaction mixture slowly, and the mixture was filtered. The filter cake was washed with EtOAc (20 mL×3), then dried under reduced pressure to give the crude product as a yellow solid (2.7 g). ESI MS: m/z 166 [M+H]+.

Workup

  1. filtrationthe mixture was filtered
  2. washThe filter cake was washed with EtOAc (20 mL×3)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-9dc5937daf074e76b280e94996e42b11
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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