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

HRID 1042338Notes

Reaction equation

HRID 1042338 reaction equation
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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-b9009fd8fd864abc8c0e1bd9efb1f714
Source dataset
uspto-grants-2013_10
Patent number
US08557849B2

Reaction notes

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