Hydrochloric Acid → HCID 66619734, compound

HRID 538531Notes

Reaction equation

HRID 538531 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([F:19])=[C:6]([CH:15]=[CH:16][C:17]=1[F:18])[O:7][CH2:8][CH:9]=[CH:10][C:11]([O:13]C)=[O:12])=[O:3].[OH-].[Na+].Cl>C(O)(C)C.O>[NH2:1][C:2]([C:4]1[C:5]([F:19])=[C:6]([CH:15]=[CH:16][C:17]=1[F:18])[O:7][CH2:8][CH:9]=[CH:10][C:11]([OH:13])=[O:12])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66619907HCID 66619907, compound

Product 1

HCID 66619734HCID 66619734, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of methyl 4-[3-(aminocarbonyl)-2,4-difluorophenoxy]-2-butenoate (1.25 g, 4.61 mmol, 1 equiv.) and NaOH (0.75 g, 18.44 mmol, 4 equiv.) in isopropanol (10 ml) and H2O (20 ml) was heated under reflux for 1 h. After cooling to r.t., the mixture was acidified with conc. HCl to pH 1. The white precipitant solid was filtered and washed with Et2O (50 ml), to give 568 mg, 48% yield, mp 187-188° C., HPLC-MS (method 1): m/z 258 [M+H]+, Rt=0.98 min. By 1H-NMR analysis it was determined to be a mixture of isomers in a ratio (3:2) E:Z.

Workup

  1. temperatureunder reflux for 1 h
  2. filtrationThe white precipitant solid was filtered
  3. washwashed with Et2O (50 ml)
  4. customto give 568 mg, 48% yield, mp 187-188° C., HPLC-MS (method 1)
  5. additiona mixture of isomers in a ratio (3:2) E

Sources & evidence

ORD record
ord-31647983d72445f487c6a5312d1b9d0a
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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