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

HRID 505960Notes

Reaction equation

HRID 505960 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:21])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[C:10]([Cl:20])=[N:9][CH:8]=1.Cl>O1CCCC1.O>[Cl:20][C:10]1[C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:12][C:7]([C:6]([OH:21])=[O:5])=[CH:8][N:9]=1

Participants

6

Reactant 3

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

Product 1

HCID 866191836-Chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acidYield 94%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithiumhydroxide monohydrate (2.41 g, 57 mmol) was added to a solution of 6-chloro-5-(4-chloro-phenyl)-nicotinic acid methyl ester (8.1 g, 29 mmol) in tetrahydrofuran (120 mL) and water (34 mL) under nitrogen at room temperature. The reaction mixture was stirred for 20 h at room temperature, poured onto ice/water (200 g), acidified with 1 N HCl (120 mL) and the whole was extracted with ethyl acetate (250 mL). The water phase was extracted twice with ethylacetate (2×200 mL), organic phases were combined, dried over MgSO4 and concentrated in vacuo. 6-chloro-5-(4-chloro-phenyl)-nicotinic acid was isolated as a colorless solid and used without further purification; 7.30 g (94% yield). m/z (ISP−): 266.1 (M−H).

Workup

  1. additionpoured onto ice/water (200 g)
  2. extractionthe whole was extracted with ethyl acetate (250 mL)
  3. extractionThe water phase was extracted twice with ethylacetate (2×200 mL), organic phases
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-20cfb91dc53847c3b64985824dda07a3
Source dataset
uspto-grants-2010_08
Patent number
US07781593B2

Reaction notes

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