Methanol → 3,5-Bis(benzyloxy)picolinic acid

HRID 1797988노트

반응식

HRID 1797988 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:23]#N)=[N:11][CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:25].[Na+].C[OH:28]>>[CH2:1]([O:8][C:9]1[C:10]([C:23]([OH:28])=[O:25])=[N:11][CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 534879943,5-Bis(benzyloxy)picolinonitrile

생성물 1

HCID 534879953,5-Bis(benzyloxy)picolinic acid

실험 절차

To a solution of 3,5-bis-benzyloxy-pyridine-2-carbonitrile, 1, (26.0 g, 82.3 mmol) in MeOH (217 mL) is added 30% w/v sodium hydroxide (320 mL) and the reaction mixture is refluxed for 16 hours. The solvent is removed under reduced pressure and the resulting suspension is acidified with conc. HCl until the pH is between 1 and 2. The precipitate that results is collected by filtration, washed with H2O (10 mL) and dried overnight in a vacuum oven to afford 30 g (quantitative) of the desired product as the hydrochloride salt. 1H NMR (250 MHz, DMSO-d6) δ ppm 8.02 (1 H, d, J=2.4 Hz), 7.29-7.53 (11 H, m), 5.96 (1 H, br s), 5.28 (4 H, s). HPLC-MS: m/z 336 [M+H]+.

후처리

  1. temperaturethe reaction mixture is refluxed for 16 hours
  2. customThe solvent is removed under reduced pressure
  3. customThe precipitate that results
  4. filtrationis collected by filtration
  5. washwashed with H2O (10 mL)
  6. customdried overnight in a vacuum oven

출처 및 근거

ORD 기록
ord-2eab7e65f86848cab200987735fc127b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343952B2

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