Methanol → Methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

HRID 1424664

Reaction equation

HRID 1424664 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH2:22]C2C=CC=CC=2)=[O:20])[C:3]=1[Cl:29].CO.C[O-].[Na+]>O>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH3:22])=[O:20])[C:3]=1[Cl:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 70495450Florpyrauxifen-benzyl

Product 1

HCID 57412076Methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate (3.00 g, 6.83 mmol) was added to CH3OH (35 mL). Sodium methoxide (25 wt % in CH3OH; 1.9 mL, 8.2 mmol) was added to the reaction mixture. and the reaction mixture was allowed to stir for 24 h. Water (50 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure to remove most of the CH3OH. The mixture was extracted with EtOAc (2×40 mL), and the combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL). Concentration of the volatiles under reduced pressure provided methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinate as a pale yellow solid (2.04 g, 88% purity by LC area).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove most of the CH3OH
  3. extractionThe mixture was extracted with EtOAc (2×40 mL)
  4. washthe combined organic layers were washed with water (40 mL) and satd sodium chloride (40 mL)

Sources & evidence

ORD record
ord-aa1e933017a648e89a8e1de269a72982
Source dataset
uspto-grants-2015_01
Patent number
US08927731B2

Linked notes

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