Dimethylformamide → 6,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinate

HRID 917359

Reaction equation

HRID 917359 reaction equation
CN(C)C=O.CS([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])(=O)=O.[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][N:22]=1.C(=O)([O-])O.[Na+]>O>[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:19])=[C:16]([F:18])[F:17])=[O:26])=[CH:23][N:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 184966-Aminonicotinic acidHCID 516892Sodium BicarbonateHCID 230203716,6-Difluoro-5-methyl-5-hexenyl methanesulfonate

Product 1

HCID 230203546,6-Difluoro-5-methyl-5-hexenyl 6-aminonicotinateYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 7 ml of N,N-dimethylformamide were dissolved 0.92 g (4.0 mmol) of 6,6-difluoro-5-methyl-5-hexenyl methanesulfonate and 0.72 g (5.2 mmol) of 6-aminonicotinic acid, followed by the addition of 1.30 g (16 mmol) of sodium hydrogencarbonate and stirring at 100° C. for 3 hours. The reaction liquid was then poured in water and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 0.85 g (yield: 78%) of 6,6-difluoro-5-methyl-5-hexenyl 6-aminonicotinate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-d887f99e52204fbf8dc28b0181e8ef2c
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Linked notes

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