Hexane → 2-(2,4-Difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chloride

HRID 232460Notes

Reaction equation

HRID 232460 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([F:21])=[CH:15][C:11]=1[C:12](O)=[O:13].S(Cl)([Cl:24])=O.CCCCCC>C(Cl)Cl.CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[C:17]([O:19][CH3:20])[C:16]([F:21])=[CH:15][C:11]=1[C:12]([Cl:24])=[O:13]

Participants

6

Reactant 3

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 138217673-Pyridinecarboxylic acid,2-[(2,4-difluorophenyl)amino]-5-fluoro-6-methoxy-

Product 1

HCID 138493482-(2,4-Difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chlorideYield 91.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

In 150 ml of methylene chloride was suspended 5.00 g of 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinic acid, and 5.98 g of thionyl chloride and 3 drops of N,N-dimethylformamide were added thereto, after which the resulting mixture was subjected to reaction under reflux for 2 hours. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 10 ml of n-hexane, after which crystals were collected by filtration to obtain 4.87 g (yield 91.7%) of 2-(2,4-difluorophenylamino)-5-fluoro-6-methoxynicotinoyl chloride having a melting point of 153°-154° C.

Workup

  1. additionwere added
  2. customafter which the resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2 hours
  4. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure
  5. customto the crystalline material thus obtained
  6. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-16c2f8eb06f748e9a474e8ca09c9415e
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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