Hydrochloric Acid → 4-(4-Chloro-2-fluorophenyl)-6-methylnicotinic acid

HRID 1398433ノート

反応式

HRID 1398433 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]=[C:10]([CH3:18])[CH:9]=2)=[C:4]([F:19])[CH:3]=1.[OH-].[Na+].Cl>CO.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]=[C:10]([CH3:18])[CH:9]=2)=[C:4]([F:19])[CH:3]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86695958Methyl 4-(4-chloro-2-fluorophenyl)-6-methylnicotinate

生成物 1

HCID 867104124-(4-Chloro-2-fluorophenyl)-6-methylnicotinic acid収率 69.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of Methyl 4-(4-chloro-2-fluorophenyl)-6-methylnicotinate (700 mg, 2.50 mmol) in MeOH (5 mL) was added NaOH (200 mg, 7.51 mmol) in water (5 mL). The reaction mixture was stirred at room temperature for 2 h. Then it was evaporated under reduced pressure and the residue obtained was adjusted to pH ˜3 by adding 1.5N HCl solution. The product was extracted with dichloromethane. The organic phase was dried over Na2SO4, and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-6-methylnicotinic acid (500 mg, 1.730 mmol, 69% crude yield) as white solid. The material was carried forward without further purification. LC/MS (ESI) m/e 266.0 [(M+H)+, calcd for C13H10ClFNO2 266.0]; LC/MS retention time (Method I): tR=1.51 min.

後処理

  1. customThen it was evaporated under reduced pressure
  2. customthe residue obtained
  3. extractionThe product was extracted with dichloromethane
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4904e28e3cab42d5a2ba626687467ea0
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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