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

HRID 1797988ノート

反応式

HRID 1797988 の反応式
[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

参加物

4

反応物 3

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

生成物 1

HCID 534879953,5-Bis(benzyloxy)picolinic acid

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-2eab7e65f86848cab200987735fc127b
出典データセット
uspto-grants-2013_01
特許番号
US08343952B2

反応ノート

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