Ammonia → Methyl 4-methoxy-2,3-dihydro-1H-indole-2-carboxylate
Reaction equation
[Mg].[CH3:2][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[C:7]([C:13]([OH:15])=[O:14])[NH:8]2.Cl.N.[CH3:18]O>>[CH3:2][O:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]([C:13]([O:15][CH3:18])=[O:14])[NH:8]2Participants
Conditions
- Temperature
- 10 °C
Procedure
119 mg (4.90 mmol) of magnesium chips are added to a solution of 500 mg (2.44 mmol) of 4-methoxy-1H-indole-2-carboxylic acid in 10 ml of methanol. The mixture is agitated for 3 hours in a bath at 10° C. and then for 1 hour at ambient temperature. 20 ml of hydrochloric acid are added at 0° C. and agitation takes place for one hour. Then a solution of ammonia 3N is added until a pH of 10 is reached and extraction takes place 3 times by 50 ml of ethyl acetate. The organic phases are dried on magnesium sulfate, filtered and concentrated under reduced pressure. The evaporation residue is purified by silica column chromatography eluting with the help of a dichloromethane/ethyl acetate mixture (98/2 then 95-5; v/v). The expected product is obtained in the form of a brown oil with a yield of 64%.
Workup
- waitfor 1 hour at ambient temperature
- customfor one hour
- extractionextraction
- customThe organic phases are dried on magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe evaporation residue is purified by silica column chromatography
- washeluting with the help of a dichloromethane/ethyl acetate mixture (98/2
Sources & evidence
- ORD record
- ord-423a90d6b49046d6b518e56aa32c56da
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872021B2
Reaction notes
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