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

HRID 607347노트

반응식

HRID 607347 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-97862cfa515847ddb37de0da9fb3120c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915443B2

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