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

HRID 912883Notes

Reaction equation

HRID 912883 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.[Sn].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 516892Sodium BicarbonateHCID 5352426Tin atomHCID 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 (TI) 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-a75375692e114f74975fb8decebff214
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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