Ethanol → 6-Ethoxy-2-pyridinamine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[N:3]=1.[CH2:9]([OH:11])[CH3:10].[OH-].[Na+]>ClCCl>[CH2:9]([O:11][C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[CH:6][CH:5]=1)[CH3:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
Introduced into a microwave tube are 500 mg (2.89 mmol) of 2-amino-6-bromopyridine, to which 2 ml of ethanol and 231 mg (5.78 mmol, 2 eq) of sodium hydroxide are added. The mixture is heated for 10 hours in a microwave oven at 170° C. The reaction medium is diluted with 50 ml of dichloromethane and then washed twice with 50 ml of water. The organic phase is concentrated to dryness and the residue is purified by chromatography over silica with, as eluent, heptane/ethyl acetate (1/1). The expected product is obtained in the form of a colourless oil.
Workup
- additionIntroduced into a microwave tube
- washwashed twice with 50 ml of water
- concentrationThe organic phase is concentrated to dryness
- customthe residue is purified by chromatography over silica with, as eluent
Sources & evidence
- ORD record
- ord-27634fa7300f49a98bb8830c44fe8199
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09050266B2
Reaction notes
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