Water → 5-(2-Chloro-5-trifluoromethyl-phenyl)-6-cyclopentyloxy-3-pyridinecarboxylic acid

HRID 1929814Notes

Reaction equation

HRID 1929814 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([O:22][CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:9]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][C:12]=2[Cl:21])[CH:10]=1)=[O:4].O.[OH-].[Na+]>O1CCOCC1>[Cl:21][C:12]1[CH:13]=[CH:14][C:15]([C:17]([F:18])([F:20])[F:19])=[CH:16][C:11]=1[C:9]1[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[N:7][C:8]=1[O:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 675053545-(2-Chloro-5-trifluoromethyl-phenyl)-6-cyclopentyloxy-3-pyridinecarboxylic acid methyl ester

Product 1

HCID 211097015-(2-Chloro-5-trifluoromethyl-phenyl)-6-cyclopentyloxy-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5-(2-Chloro-5-trifluoromethyl-phenyl)-6-cyclopentyloxy-3-pyridinecarboxylic acid methyl ester (0.27 g, 0.7 mmol) was dissolved in dioxane (6 mL). Water (6 mL) and sodium hydroxide solution (2 mL, 2N) was added and the mixture was boiled with stirring for 2.5 h, cooled to room temperature and partitioned between diethyl ether and hydrochloric acid (1N). Organic phases were pooled, dried with Na2SO4 and the solvent was evaporated. The residue, 0.27 g of the title compound as a orange-yellow solid was introduced into the next step without purification, MS (ISP) 386.5 (M+H)+.

Workup

  1. custompartitioned between diethyl ether and hydrochloric acid (1N)
  2. dry with materialdried with Na2SO4
  3. customthe solvent was evaporated
  4. additionThe residue, 0.27 g of the title compound as a orange-yellow solid was introduced into the next step without purification, MS (ISP) 386.5 (M+H)+

Sources & evidence

ORD record
ord-e27288a8c457411398d5171955b682f2
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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