Hydrochloric Acid → HCID 68863615, compound

HRID 493571Notes

Reaction equation

HRID 493571 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-])[C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(OC(=O)C)(=[O:17])C.FC(F)F.Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([CH2:13][OH:17])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68864703HCID 68864703, compoundHCID 86601918HCID 86601918, compound

Product 1

HCID 68863615HCID 68863615, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 5-chloro-2-methylnicotinate 1-oxide (step 3, 4.1 g, 19 mmol) in dichloromethane (100 ml) was added trifluoromethane acetic acid anhydride (4 ml) at room temperature and the reaction mixture was stirred for 3 days. The reaction mixture was added 2 N hydrochloric acid solution (30 ml) with stirring. After 30 min, the whole mixture was extracted with dichloromethane. The organic phase was washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (20/1 to 4/1) to afford 840 mg (20%) of the title compound:

Workup

  1. stirringwith stirring
  2. waitAfter 30 min
  3. extractionthe whole mixture was extracted with dichloromethane
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (20/1 to 4/1)

Sources & evidence

ORD record
ord-5e84df618959420587faa3c075060dc1
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

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