Nitrogen → methyl 2-[3-(1-pyridin-3-ylethenyl)-1H-indol-2-yl]acetate
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][C:11]([O:13][CH3:14])=[O:12].[C:15]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)(=O)[CH3:16].OS(O)(=O)=O.N#N.[NH4+].[OH-]>CO>[C:11]([CH2:10][C:2]1[NH:1][C:9]2[C:4]([C:3]=1[C:15]([C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[CH2:16])=[CH:5][CH:6]=[CH:7][CH:8]=2)([O:13][CH3:14])=[O:12]Participants
7
Procedure
A solution of 6.13 g (0.032 m) of methyl indole-2 acetate, 7.16 g (7.0 mL, 0.059 m) of 3-acetylpyridine, and 10 mL of concentrated H2SO4 in 200 mL of dry MeOH was refluxed for 2 hours in an atmosphere of N2. The clear red solution was poured onto 600 g of ice. It was made alkaline with NH4OH and extracted with 2×500 mL portions of ether. The ether solution was washed with H2O, dried, and concentrated to dryness. The residue was triturated with hexane-ether (1:1), and the crystals that formed were collected and dried; wt 8.0 g; mp 154°-157° C. (lit. mp 160°-161° C.). The material was suitable for the next step. An additional 110 mg separated from the ether-hexane filtrate. Total yield 8.17 g.
Workup
- extractionextracted with 2×500 mL portions of ether
- washThe ether solution was washed with H2O
- customdried
- concentrationconcentrated to dryness
- customThe residue was triturated with hexane-ether (1:1)
- customthe crystals that formed
- customwere collected
- customdried
- customAn additional 110 mg separated from the ether-hexane filtrate
Sources & evidence
- ORD record
- ord-03e1526010d745f9adf6ba163e159a4f
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04851417
Reaction notes
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