Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate → HCID 22677347, compound

HRID 1837460Notes

Reaction equation

HRID 1837460 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:3]=1[Cl:20]>C(O)CCCCCCCCC.C[O-].[Ti+4].C[O-].C[O-].C[O-]>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=2)[N:5]=[C:4]([C:16]([O:18][CH2:19][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:9][CH2:10][CH2:11][CH3:12])=[O:17])[C:3]=1[Cl:20]

Participants

4

Reactant 1

HCID 22677303Methyl 4-amino-5-fluoro-3-chloro-6-(4-chlorophenyl)picolinate

Product 1

HCID 22677347HCID 22677347, compoundYield 173.4%

Reagents, catalysts & solvents 2

HCID 164767Titanium tetra(methanolate)CatalystHCID 81741-DecanolSolvent

Procedure

Methyl 4-amino-3-chloro-5-fluoro-6-(4-chlorophenyl)pyridine-2-carboxylate (0.545 g, 1.73 mmol) was suspended in decanol (20 mL) and titanium methoxide (0.029 g, 1.73 mmol) was added and the mixture heated under reflux for five hours. The reaction mixture was concentrated and the residue dissolved in ethyl acetate (100 mL) and washed with water (100 mL) and saturated sodium bicarbonate solution (100 mL). The organic phase was dried (MgSO4) and concentrated to give decyl 4-amino-3-chloro-5-fluoro-6-(4-chlorophenyl)pyridine-2-carboxylate (0.67 g, 1.5 mmol), mp 62-63° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for five hours
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue dissolved in ethyl acetate (100 mL)
  5. washwashed with water (100 mL) and saturated sodium bicarbonate solution (100 mL)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c606d8ccca6442c8b6ccd43353504e9f
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

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