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

HRID 1398288ノート

反応式

HRID 1398288 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a5a406f56ef4ec79cd4bbe4d4117485
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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