Acetyl chloride → HCID 90408564, compound

HRID 516551Notes

Reaction equation

HRID 516551 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([F:18])[C:12]=2[F:19])[N:8]=[C:7]([C:20]([O:22][CH3:23])=[O:21])[C:6]=1[Cl:24])(=O)C.C(Cl)(=O)C>CO>[NH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[C:13]([F:18])[C:12]=2[F:19])[N:8]=[C:7]([C:20]([O:22][CH3:23])=[O:21])[C:6]=1[Cl:24]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90408626HCID 90408626, compound

Product 1

HCID 90408564HCID 90408564, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-acetamido-6-(4-bromo-2,3-difluorophenyl)-3-chloropicolinate (0.515 g, 1.227 mmol) was suspended in methanol (20 mL) and acetyl chloride (1.559 mL, 21.93 mmol) was added dropwise. The reaction mixture was stirred overnight at room temperature and concentrated under vacuum. The residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate solution. The organic phase was concentrated onto silica gel and purified by flash chromatography (SiO2, eluting with 5-60% ethyl acetate in hexanes) to provide the title compound as a white solid (0.231 g, 55.8%).

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was partitioned between ethyl acetate and 5% aqueous sodium bicarbonate solution
  3. concentrationThe organic phase was concentrated onto silica gel
  4. custompurified by flash chromatography (SiO2, eluting with 5-60% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-aabb02ba409d4de1a521a5510043e5aa
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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