Hydrochloric Acid → 2-Chloro-5-ethyl-nicotinic acid

HRID 2100545Notes

Reaction equation

HRID 2100545 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([CH2:12][CH3:13])[CH:9]=[N:8][C:7]=1[Cl:14].ClCCl.Cl>C1COCC1>[Cl:14][C:7]1[N:8]=[CH:9][C:10]([CH2:12][CH3:13])=[CH:11][C:6]=1[C:5]([OH:15])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 110634332-Chloro-5-ethyl-nicotinic acid methyl ester

Product 1

HCID 200786802-Chloro-5-ethyl-nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1 N aqueous LiOH solution (3.3 ml, 3.3 mmol) was added to a solution of 2-chloro-5-ethyl-nicotinic acid methyl ester (325 mg, 1.6 mmol; T. Y. Zhang, E. F. V. Scriven, WO 9318005 A2) in THF (3.3 ml). The reaction mixture was stirred for 3 h at ambient temperature, poured onto ice water/isopropyl acetate 1/1 and acidified with 1 N aqueous HCl solution. The layers were separated and the aqueous layer was extracted two times with isopropyl acetate. The combined extracts were washed with brine, dried over sodium sulfate and the solvent was removed under reduced pressure to give 2-chloro-5-ethyl-nicotinic acid as white solid (292 mg, 1.57 mmol; 97%) which was used in the next step without further purification. MS: m/e=184.1 [M−H−].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted two times with isopropyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-09fb83ea89024c4ea942a5bf4d3b3767
Source dataset
uspto-grants-2009_08
Patent number
US07572801B2

Reaction notes

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