Ethanol → HCID 60136073, compound

HRID 2249398Notes

Reaction equation

HRID 2249398 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([O:20][CH3:21])=[O:19])[C:3]=1[Cl:22].[CH2:23](O)C>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([O:20][CH2:21][CH3:23])=[O:19])[C:3]=1[Cl:22]

Participants

4

Reactant 2

HCID 702EthanolHCID 16656802Halauxifen-methyl

Product 1

HCID 60136073HCID 60136073, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

To a solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, methyl ester (200 mg, 0.9 mmol) in ethanol (5 mL) was added a catalytic amount of titanium tetraisopropoxide and the solution heated under reflux for 2 hours. The solution was cooled and partitioned between ethyl acetate (10 mL) and water (10 mL) and the organic phase was dried (sodium sulfate) and concentrated. The residue was passed over a plug of silica gel (1:1 ethyl acetate: hexanes) to give 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid, ethyl ester (150 mg. 0.6 mmol): mp 74-75° C.

Workup

  1. temperaturethe solution heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe solution was cooled
  4. custompartitioned between ethyl acetate (10 mL) and water (10 mL)
  5. dry with materialthe organic phase was dried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-961eeafbb1cc4391b8ef9aaece632fb7
Source dataset
uspto-grants-2008_01
Patent number
US07314849B2

Reaction notes

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