Hydrochloric Acid → Methyl 3-(3-methyl-1-{3-(phenyl)propyl}-1H-indol-6-yl)-3-nitromethyl-propionate
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=2)[N:4]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=1.CN(C)C(=N)N(C)C.Cl.[N+:35]([CH3:38])([O-:37])=[O:36]>>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]([CH2:38][N+:35]([O-:37])=[O:36])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:9]=2)[N:4]([CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:3]=1Participants
Conditions
- Temperature
- 65 °C
Procedure
A stirred solution of methyl 3-(3-methyl-1-{3-(phenyl)propyl}-1 H-indol-6-yl)-propenoate (0.263 g, Reference Example 39) in nitromethane (5 ml) was treated with tetramethylguanidine (0.091 g). The mixture was heated to 65° C. for 2 hours then treated with a further aliquot of tetramethylguanidine (0.091 g). After heating at 65° C. for a further hour the reaction mixture was cooled to room temperature then poured into hydrochloric acid (20 ml, 1N) then extracted three times with ethyl acetate (25 ml). The combined extracts were dried over magnesium sulphate then evaporated. The residue was subjected to preparative layer chromatography on silica using a mixture of ethyl acetate and hexane (1:2, v/v) as eluent to yield the title compound (0.296 g).
Workup
- temperatureAfter heating at 65° C. for a further hour the reaction mixture
- temperaturewas cooled to room temperature
- extractionthen extracted three times with ethyl acetate (25 ml)
- dry with materialThe combined extracts were dried over magnesium sulphate
- customthen evaporated
- additiona mixture of ethyl acetate and hexane (1:2
Sources & evidence
- ORD record
- ord-63b612fb60474480b1c4a2a6478134f1
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06303600B1
Reaction notes
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