1,2-Dichloroethane → HCID 86625527, compound

HRID 2265973Notes

Reaction equation

HRID 2265973 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[C:5](C(O)=O)=[CH:4][N:3]=1.Cl.[CH3:16][NH:17][O:18][CH3:19].CN1CCOCC1.C(Cl)CCl>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([N:17]([CH3:16])[O:18][CH3:19])=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:10]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27833826-Chloro-4-(trifluoromethyl)nicotinic acid

Product 1

HCID 86625527HCID 86625527, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-chloro-4-trifluoromethyl-nicotinic acid (0.9 g, 3.99 mmol) in methylene chloride were added N,O-dimethylhydroxylamine HCl (0.39 g, 1.0 eq), NMM (0.44 ml), and EDC (0.768 g) at 0° C. and the reaction mixture was stirred at 0° C. for 2 hrs. The reaction mixture was extracted with methylene chloride, and washed with water and brine. The organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc=4/1) to give the product (0.824 g, 76.9%).

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by column chromatography (Hex/EtOAc=4/1)

Sources & evidence

ORD record
ord-87fbfa72fa6c4388b79a5ddb4786f307
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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