Ethylenediamine → 6-Amino-4-methylnicotinonitrile
Reaction equation
Br[C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:10]([Cu])#[N:11].C(N)CN>CC(N(C)C)=O>[NH2:8][C:5]1[CH:4]=[C:3]([CH3:9])[C:2]([C:10]#[N:11])=[CH:7][N:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 170 °C
Procedure
A mixture of 5-bromo-4-methyl-pyridin-2-ylamine (500 mg, 2.67 mmol), CuCN (478 mg, 5.34 mmol) and DMA (2 mL) was stirred under nitrogen for 20 h at 170° C. The reaction mixture was cooled and added to 50 mL of a 20% aqueous solution of ethane-1,2-diamine. The layers were separated and the aqueous layer was extracted 3× with EtOAc. The combined organics were washed with water followed by brine and dried over MgSO4. Concentration in vacuo afforded compound 851A (309 mg, 87%) as a white solid.
Workup
- temperatureThe reaction mixture was cooled
- customThe layers were separated
- extractionthe aqueous layer was extracted 3× with EtOAc
- washThe combined organics were washed with water
- dry with materialdried over MgSO4
- concentrationConcentration in vacuo
Sources & evidence
- ORD record
- ord-f1cda6e7b855453aba081b91d743fa7d
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07655689B2
Reaction notes
Loading…