Diazomethane → methyl 1H-indole-4-carboxylate
Reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[N+](=[CH2:15])=[N-]>CCOCC>[CH3:15][O:11][C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a 0° C. solution of indole-4-carboxylic acid (1.00 g, 6.21 mmol) in ether (60 mL) was added diazomethane (0.3M solution in ether, 24.8 mL, 7.45 mmol) and the reaction mixture was stirred for 0.5 hours at 0° C. An additional 20 mL of diazomethane solution was then added and stirring was continued for 1 hour at 0° C. The reaction mixture was quenched with formic acid (1.0 mL) and concentrated in vacuo to give 4-methoxycarbonylindole (1.1 g) as an off white powder.
Workup
- stirringstirring
- waitwas continued for 1 hour at 0° C
- customThe reaction mixture was quenched with formic acid (1.0 mL)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c9fd2a90a23a46448a21c62716522421
- Source dataset
- uspto-grants-1996_01
- Patent number
- US05486525
Reaction notes
Loading…