Triethylamine → N-Methoxy-N-methyl-1H-indole-3-carboxamide
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=O)=[CH:2]1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:20][NH:21][O:22][CH3:23].C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH3:23][O:22][N:21]([CH3:20])[C:10]([C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)=[O:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Indole-3-carboxylic acid (2.50 g, 0.0155 mol) was suspended in dichloromethane (60 ml) and treated with oxalyl chloride (1.62 ml, 0.0186 mol), followed by a drop of dry DMF. The reaction mixture was then stirred at room temperature overnight, before being evaporated under reduced pressure and dried in vacuo. The product was then redissolved in dichloromethane (50 ml) and added slowly to a solution of N,O-dimethylhydroxylamine hydrochloride (1.59 g, 0.0163 mol) in dichloromethane (50 ml) containing triethylamine (4.53 ml, 0.0326 mol) under argon. The resultant mixture was then stirred at room temperature for 2 h, before being washed with water, followed by aq. NaHCO3. The organic layer was then dried (Na2SO4), evaporated under reduced pressure and dried in vacuo to yield the title compound as white solid (2.46 g, 78%).
Workup
- custombefore being evaporated under reduced pressure
- customdried in vacuo
- dissolutionThe product was then redissolved in dichloromethane (50 ml)
- washbefore being washed with water
- dry with materialThe organic layer was then dried (Na2SO4)
- customevaporated under reduced pressure
- customdried in vacuo
Sources & evidence
- ORD record
- ord-fa2d91cd8e7f41ff8cae7dff4cd848fe
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114329
Reaction notes
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