Sodium Hydroxide → 5-(2-Phenyleth-1-Ynyl)Nicotinic Acid

HRID 391509

反応式

HRID 391509 の反応式
C([O:3][C:4](=[O:19])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+]>CO.O>[C:13]1([C:12]#[C:11][C:9]2[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=2)[C:4]([OH:19])=[O:3])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 2779231Ethyl 5-(2-phenyleth-1-ynyl)nicotinate

生成物 1

HCID 27792365-(2-Phenyleth-1-Ynyl)Nicotinic Acid収率 95.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of 5-phenylethynyl-nicotinic acid ethyl ester (1.17 g, 4.64 mmol) in methanol (10 mL) was added 5 N aqueous sodium hydroxide (2 mL, 10 mmol). The mixture was stirred at room temperature for approximately 20 h, before the reaction mixture was diluted with water (3 mL) and extracted with hexanes/EtOAc (95/5) (10 mL). The aqueous solution was acidified with 1 N HCl to pH 4. The white precipitate that formed was collected by filtration, washed with water (2 mL), and dried under vacuum to provide the title compound as a white solid (987 mg, yield 95%). 1H NMR (300 MHz, d6-DMSO) δ 9.02 (d, J=1.8 Hz, 1H), 8.94 (d, J=2.4 Hz, 1H), 8.34 (dd, J=1.8, 2.4 Hz, 1H), 7.63-7.60 (m, 2H), 7.48-7.44 (m, 3H); ESI-MS m/z 223.9 (M+H)+.

後処理

  1. extractionextracted with hexanes/EtOAc (95/5) (10 mL)
  2. customThe white precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water (2 mL)
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-34d9dcee62ae4decbe0215cb05936d10
出典データセット
uspto-grants-2013_02
特許番号
US08383825B2

関連ノート

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