N,N,N',N'-Tetramethylethylenediamine → 5,8-dimethylindeno[2,1-b]indol-6(5H)-one
Reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:3]1.CN(CCN(C)C)C.[Li]CCCC.CN(C)[C:33](=O)[O:34]CC.[NH4+].[Cl-]>CCOCC.CCCCCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]2[C:11]3[C:12]([C:33](=[O:34])[C:3]1=2)=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=3Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -40 °C
Procedure
A solution of 2.19 g (0.00991 mol) of 1-methyl-3-(4-methylphenyl)-1H-indole and 3.24 mL (0.0218 mol) of TMEDA in 30 mL of ether was treated with 13.6 mL (0.0218 mol) of 1.6M BuLi in hexane under stirring at −40° C. Then the reaction mixture was allowed to warm up to r.t. and stirred for 4 h. The reaction mixture was cooled to −60° C. and treated with 1.16 g (0.00991 mol) ethyl N,N-dimethylcarbamate in 5 mL of ether. Then the reaction mixture was allowed to warm up to r.t. and was stirred overnight. Resulting mixture was treated with 50 mL of 10% aqueous NH4Cl. The violet precipitate was separated, washed twice with water and dried. Yield 1.04 g (42%).
Workup
- temperatureto warm up to r.t.
- stirringstirred for 4 h
- temperatureThe reaction mixture was cooled to −60° C.
- temperatureto warm up to r.t.
- stirringwas stirred overnight
- customResulting mixture
- customThe violet precipitate was separated
- washwashed twice with water
- customdried
Sources & evidence
- ORD record
- ord-d0bea804a29e485190ab03ca9a96cc03
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07253292B2
Reaction notes
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