Water → Methyl 3-amino-6-methoxy-5-(trifluoromethyl)picolinate

HRID 574232Notes

Reaction equation

HRID 574232 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([OH:16])=[O:15])=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.OS(O)(=O)=O.O.[C:23]([O-])(O)=O.[Na+]>CO>[NH2:1][C:2]1[C:3]([C:14]([O:16][CH3:23])=[O:15])=[N:4][C:5]([O:12][CH3:13])=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 584423203-Amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid

Product 1

HCID 71743539Methyl 3-amino-6-methoxy-5-(trifluoromethyl)picolinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Amino-6-methoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (Int. B) 5.5 g, 23.29 mmol) was dissolved in MeOH (90 ml). H2SO4 (6.21 ml, 116 mmol) was added dropwise and the solution was heated to reflux for 4 hours. The reaction mixture was reduced in vacuo to approx. 15 ml and water (15 ml) was added. The pH was adjusted to pH 9 by careful addition of solid NaHCO3. Water (100 ml) was added and the mixture was extracted with DCM. The combined organic extracts were concentrated in vacuo to afford the title compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 4 hours
  3. additionwas added
  4. extractionthe mixture was extracted with DCM
  5. concentrationThe combined organic extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-38db66b0176e40dba6a499540d75f996
Source dataset
uspto-grants-2015_05
Patent number
US09034879B2

Reaction notes

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