Sodium Hydroxide → HCID 86668308, compound

HRID 75102Notes

Reaction equation

HRID 75102 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([O:12]C)=[O:11])[C:3]=1[CH:14]=[CH2:15].[OH-].[Na+]>CO.CC(C)=O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([Cl:9])[N:5]=[C:4]([C:10]([OH:12])=[O:11])[C:3]=1[CH:14]=[CH2:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86668309Methyl 4-amino-6-chloro-5-fluoro-3-vinylpicolinate

Product 1

HCID 86668308HCID 86668308, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

To a solution of methyl 4-amino-6-chloro-5-fluoro-3-vinylpicolinate (0.150 g, 0.650 mmol) in methanol (3.25 mL) and acetone (3.25 mL) was added sodium hydroxide (0.078 g, 1.951 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was concentrated, diluted with ethyl acetate, and washed with 1N HCl. The organic phase was dried over Na2SO4, filtered, concentrated, and dried under high vacuum to afford the title compound (89 mg, 0.411 mmol, 63.2% yield) as a white solid: mp 164-166° C.; 1H NMR (400 MHz, DMSO) δ 13.34 (s, 1H), 6.67 (s, 2H), 6.67 (dd, J=17.7, 11.5 Hz, 3H), 5.53 (dd, J=10.4, 1.2 Hz, 1H), 5.49 (dd, J=16.7, 1.1 Hz, 1H); 19F NMR (376 MHz, DMSO) δ −142.00 (s); ESIMS m/z 215 ([M−H)−].

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with 1N HCl
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-2cfbd132fc7e4bb98a04802b9befe011
Source dataset
uspto-grants-2014_09
Patent number
US08835409B2

Reaction notes

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