1,2-Dichloroethane → HCID 58307476, compound

HRID 222797Notes

Reaction equation

HRID 222797 reaction equation
FC(F)(F)C(O)=O.ClCCCl.C([O:16][C:17]([C:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][C:22](=[O:29])[N:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:20]=1[CH3:36])=[O:18])(C)(C)C>>[CH3:36][C:20]1[N:21]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:22](=[O:29])[CH:23]=[C:24]([C:25]([F:26])([F:28])[F:27])[C:19]=1[C:17]([OH:18])=[O:16]

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 58307483HCID 58307483, compound

Product 1

HCID 58307476HCID 58307476, compound

Procedure

Trifluoroacetic acid (100 uL, 1 mmol) in 1,2-dichloroethane (200 uL, 2 mmol) was added to 2-methyl-6-oxo-1-phenyl-4-trifluoromethyl-1,6-dihydro-pyridine-3-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol). The obtained solution was stirred at r.t. overnight and evaporated. The residue was partitioned between 2M NaOH (4 mL) ethyl acetate (2×2 mL) to remove traces of the unreacted ester. The aqueous phase was acidified and the product extracted with ethyl acetate (2×3 mL). The combined organic solution was washed with brine, dried (MgSO4) and evaporated, yield 19.4 mg, 50%. LC-MS (m/z) 298.4 (MH+); tR=0.80 (method C).). 1H NMR (500 MHz, DMSO-d6): 1.99 (s, 3H, Me), 3.56 (br., CO2H+H2O), 6.86 (s, 1H, C5-H), 7.36 (d, J=7.3 Hz, 2H, two ortho-H of Ph), 7.50 (t, J=7.4 Hz, 1H, para-H of Ph), 7.56 (t, J=7.5 Hz, 2H, two meta-H of Ph).

Workup

  1. customevaporated
  2. customThe residue was partitioned between 2M NaOH (4 mL) ethyl acetate (2×2 mL)
  3. customto remove traces of the unreacted ester
  4. extractionthe product extracted with ethyl acetate (2×3 mL)
  5. washThe combined organic solution was washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-2ea50eebe8d04c4d9ead8b5b6cff2da4
Source dataset
uspto-grants-2012_06
Patent number
US08207347B2

Reaction notes

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