Sodium Bicarbonate → N2,N2-Dimethyl-2,3-pyridinediamine
Reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[C:8]([N+:9]([O-])=O)=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])(O)=O.[Na+]>CCO>[NH2:9][C:8]1[C:3]([N:2]([CH3:12])[CH3:1])=[N:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A stirred mixture of the product from Step 1 (1.05 g, 0.00628 mol), stannous chloride dihydrate (7.09 g, 0.03141 mol) and absolute EtOH (13.9 ml), under nitrogen, was warmed to 80° C. during 30 minutes and kept at that temperature for an additional 30 minutes. The mixture was cooled and kept at ambient temperature for 1 hour. It was then poured onto ice (200 ml), treated slowly with solid NaHCO3 (2.88 g) and adjusted to pH 8 with saturated NaHCO3. This mixture was extracted with EtOAc; the extract was washed with water, dried (Na2SO4) and concentrated to give the titled product (0.738 g), a dark oil.