Dimethylformamide → 3-Amino-2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine

HRID 1696963Notes

Reaction equation

HRID 1696963 reaction equation
[NH2:1][C:2]1[C:3]([CH3:18])=[CH:4][C:5]([O:8][CH:9]([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=1.CN(C)C=O.[Cl:24]N1C(=O)CCC1=O>O>[NH2:1][C:2]1[C:7]([Cl:24])=[N:6][C:5]([O:8][CH:9]([C:10]([F:11])([F:12])[F:13])[C:14]([F:17])([F:15])[F:16])=[CH:4][C:3]=1[CH3:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 860624455-Amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine

Product 1

HCID 231500063-Amino-2-chloro-4-methyl-6-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 5-amino-4-methyl-2-(2,2,2-trifluoro-1-trifluoromethylethoxy)pyridine was introduced to 10 ml of N,N-dimethylformamide, and 0.56 g of N-chlorosuccinic acid imide was added thereto at room temperature. The resulting solution was heated to 60 degree centigrade, stirred for 1 hour, and then poured into water and extracted with ethyl acetate. The solution was dried over anhydrous magnesium sulfate, and then the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane:ethyl acetate=10:1) to obtain 0.50 g of the desired product (Yield: 44%) as brown oil.

Workup

  1. additionwas added
  2. customat room temperature
  3. temperatureThe resulting solution was heated to 60 degree centigrade
  4. extractionextracted with ethyl acetate
  5. dry with materialThe solution was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under a reduced pressure
  7. customto obtain a residue
  8. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53dbf46c531f4f47aa1a8c0f5831feb3
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

Loading…