Dimethylformamide → 4-Chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one

HRID 2300033Notes

Reaction equation

HRID 2300033 reaction equation
[OH:1][C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=O)[C:3]=1[C:11]([C:13]1[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)=[O:12].CN(C)C=O.C(Cl)(=O)C([Cl:32])=O>>[Cl:32][C:4]1[CH:5]2[CH2:9][CH:8]([CH2:7][CH2:6]2)[C:2](=[O:1])[C:3]=1[C:11]([C:13]1[C:14]([CH3:23])=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=1)=[O:12]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178432826HCID 178432826, compound

Product 1

HCID 183742654-Chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-oneYield 90%

Conditions

Temperature
0 °C

Procedure

20.15 g (0.062 mo l) of 4-hydroxy-3-(2-methyl-6-trifluoromethyipyridine-3carbonyl)-bicyclo[3.2.1]oct-3-en-2-one are suspended in 50 ml of oxalyl chloride, and 0.1 ml of dimethylformamide are added dropwise. After the intensive evolution of gas has ceased, the mixture is kept at a bath temperature of 45° C. for another 1.5 hours and then evaporated, and the residue is suspended in a little ethyl acetate and admixed with stirring at 0° C. with hexane. Filtration gives 19.19 g (90% of theory) of 4-chloro-3-(2-methyl-6-trifluoromethyl-pyridine-3-carbonyl)bicyclo[3.2.1]oct-3-en-2-one of m.p. 137-138° C.

Workup

  1. customthe mixture is kept at a bath
  2. customevaporated
  3. filtrationFiltration

Sources & evidence

ORD record
ord-ec6f9705d76845c8a4a24dd22e646c8d
Source dataset
uspto-grants-2002_12
Patent number
US06498125B2

Reaction notes

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