Sodium Bicarbonate → HCID 178498502, compound

HRID 922803Notes

Reaction equation

HRID 922803 reaction equation
[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1/[N:9]=[C:10](\[CH2:15][C:16]([O:18]C)=O)/[C:11]([O:13][CH3:14])=[O:12].CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C([O-])(O)=O.[Na+]>>[F:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[N:9]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:15]=[C:16]2[OH:18]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidHCID 178500753HCID 178500753, compound

Product 1

HCID 178498502HCID 178498502, compoundYield 92.7%

Conditions

Temperature
50 °C

Procedure

A mixture of (E)-dimethyl 2-(2-fluoro-3-methylphenylimino)succinate (7-14, 14.59 g, 54.6 mmol) and Eaton's reagent (52.0 mL, 328 mmol) was heated at 50° C. for 1 h. After cooling to room temperature, the mixture was added slowly to a cold sat. NaHCO3 solution (gas released!), followed by EtOAc extraction (twice). The combined organic fractions were washed with brine, dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure to afford methyl 8-fluoro-4-hydroxy-7-methylquinoline-2-carboxylate (7-15, 11.9 g). LRMS m/z (M+H)+ 236.2 found, 236.1 required.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionfollowed by EtOAc extraction (twice)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-627aa250bee345648a22b604895c7205
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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