Ethanol → 6-Ethoxy-2-pyridinamine

HRID 2170000Notes

Reaction equation

HRID 2170000 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

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

  1. additionIntroduced into a microwave tube
  2. washwashed twice with 50 ml of water
  3. concentrationThe organic phase is concentrated to dryness
  4. 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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