Methanol → 4-(4-Chloro-2-fluorophenyl)nicotinic acid

HRID 1398288노트

반응식

HRID 1398288 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1.CO.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][CH:9]=2)=[C:4]([F:18])[CH:3]=1

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86695906Methyl 4-(4-chloro-2-fluorophenyl)nicotinate

생성물 1

HCID 866959074-(4-Chloro-2-fluorophenyl)nicotinic acid수율 63.4%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a solution of methyl 4-(4-chloro-2-fluorophenyl)nicotinate (15 g, 56.5 mmol) (as prepared in Ex 1, Part B) in a solvent mixture of methanol (150 mL) and water (150 mL) cooled to 0° C. was added sodium hydroxide (9.03 g, 226 mmol) and the mixture was warmed to room temperature and stirred for 1 h. The reaction mixture was concentrated under reduced pressure and pH of the resultant aqueous solution was adjusted to pH=4 using 1.5 N Hydrochloric acid during which time the product crashed out as a solid. Filtration of the mixture provided 4-(4-chloro-2-fluorophenyl)nicotinic acid (9 g, 35.8 mmol, 63% yield) as an off white solid. LC/MS (ESI) m/e 252.0 [(M+H)+, calcd for C12H8ClFNO2 252.1]; LC/MS retention time (method A): tR=0.97 min.

후처리

  1. temperaturethe mixture was warmed to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure and pH of the resultant aqueous solution
  3. filtrationFiltration of the mixture

출처 및 근거

ORD 기록
ord-1a5a406f56ef4ec79cd4bbe4d4117485
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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