Potassium Hydroxide → 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine

HRID 1042338ノート

反応式

HRID 1042338 の反応式
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([O:14][N:15]=[C:16]([C:23]2[N:27]([CH3:28])[N:26]=[N:25][N:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13])[N:7]=1)=O.[OH-].[K+]>C(O)C>[CH3:28][N:27]1[C:23]([C:16](=[N:15][O:14][CH:12]([C:8]2[N:7]=[C:6]([NH2:5])[CH:11]=[CH:10][CH:9]=2)[CH3:13])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:24][N:25]=[N:26]1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 866499712,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide

生成物 1

HCID 866499726-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine収率 68.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirred solution of 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide (19.7 g, 48.3 mmol, 1 eq.) in 200 ml of ethanol, was added potassium hydroxide (88.4 g, 1.57 mol, 32.6 eq.). The reaction mixture was stirred and heated to reflux for 4 hrs. After evaporation of the solvent, The residue was taken up with water (300 ml) and extracted with EtOAc (100 ml). The aqueous layer was separated and extracted twice with EtOAc (100 ml). The organics were combined, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine (10.7 g, 90% pure, 61% yield)

後処理

  1. temperatureheated
  2. temperatureto reflux for 4 hrs
  3. customAfter evaporation of the solvent
  4. extractionextracted with EtOAc (100 ml)
  5. customThe aqueous layer was separated
  6. extractionextracted twice with EtOAc (100 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-b9009fd8fd864abc8c0e1bd9efb1f714
出典データセット
uspto-grants-2013_10
特許番号
US08557849B2

反応ノート

読み込み中…