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

HRID 1099607노트

반응식

HRID 1099607 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-3ba4d682f66c46419216a84ff559d230
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143410B2

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