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

HRID 2100545ノート

反応式

HRID 2100545 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 200786802-Chloro-5-ethyl-nicotinic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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−].

後処理

  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

出典と根拠

ORDレコード
ord-09fb83ea89024c4ea942a5bf4d3b3767
出典データセット
uspto-grants-2009_08
特許番号
US07572801B2

反応ノート

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