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

HRID 2100545노트

반응식

HRID 2100545 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 200786802-Chloro-5-ethyl-nicotinic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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−].

후처리

  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

출처 및 근거

ORD 기록
ord-09fb83ea89024c4ea942a5bf4d3b3767
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572801B2

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