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

HRID 1772032Notes

Reaction equation

HRID 1772032 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-976468acb9fa4f78aeda526a0803f86f
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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