Hydrochloric Acid → 6-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

HRID 1929798Notes

Reaction equation

HRID 1929798 reaction equation
C[O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[C:7]([Cl:17])=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:17][C:7]1[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:9][C:4]([C:3]([OH:18])=[O:2])=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 73013037HCID 73013037, compound

Product 1

HCID 866191836-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-5-(4-chloro-phenyl)-nicotinic acid methyl ester (30.9 g, 0.11 mol) was dissolved in a mixture of tetrahydrofuran (750 mL) and water (250 mL). Lithiumhydroxid monohydrate (13.8 g, 0.33 mol) was added and the mixture was stirred and heated at reflux-temperature for 1 h. After cooling to room temperature the mixture was acidified with hydrochloric acid (2N, 240 mL) and extracted with methyl-t-butylether. Organic phases were pooled, dried with MgSO4 and the mixture concentrated in vacuo. The title compound crystallized from the concentrated solution as a white solid (quant.); MS (ISP) 266.0 (M−H)

Workup

  1. temperatureheated
  2. temperatureat reflux-temperature for 1 h
  3. extractionextracted with methyl-t-butylether
  4. dry with materialdried with MgSO4
  5. concentrationthe mixture concentrated in vacuo
  6. customThe title compound crystallized from the concentrated solution as a white solid (quant.)

Sources & evidence

ORD record
ord-ef7588de671a451d9772ec1a7b923b7d
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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