Dimethylformamide → 5-(Trifluoromethyl)pyridine-2,3-diamine

HRID 730823Notes

Reaction equation

HRID 730823 reaction equation
[N+:1]([C:4]1[C:5]([NH2:14])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.O.O.[Sn](Cl)Cl.CN(C=O)C.C([O-])(O)=O.[Na+]>CCOC(C)=O>[F:13][C:10]([F:11])([F:12])[C:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:14])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 106083913-Nitro-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 102144255-(Trifluoromethyl)pyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-nitro-5-trifluoromethyl-pyridin-2-ylamine from step (a) above (1.2 g, 5.59 mmol), tin (II) chloride dihydrate (3.9 g, 17.3 mmol, Aldrich), and DMF (19 mL) was heated to 60° C. for 4 h. The reaction mixture was cooled to room temperature and NaHCO3 (150 mL) was added. The mixture was stirred for 0.5 h, diluted with EtOAc (300 mL), stirred for 0.5 h and filtered. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×300 mL). The combined organic extracts were dried over MgSO4 and filtered. The solvent was removed in vacuo to give the title compound, which was used in the next step without additional purification. MS (ESI, positive ion) m/z: 178 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringstirred for 0.5 h
  3. filtrationfiltered
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc (2×300 mL)
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-db9c21308ced466680cdb4666aa20266
Source dataset
uspto-grants-2009_09
Patent number
US07582761B2

Reaction notes

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