5-(1,1-Dimethylethyl)-1H-indole-2-carboxylic acid → 5-(tert-Butyl)-1H-indole
Reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](C(O)=O)=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>N1C2C(=CC=CC=2)C=CC=1>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 220 °C
Procedure
A mixture of 5 -tert-butylindole-2-carboxylic acid (2.3 g) and cupper powder (0.46 g) in quinoline (20 ml) was stirred at 220° C. for 1 hour. After cooling, the reaction mixture was partitioned between diluted hydrochloric acid and diethyl ether. The ether layer was washed successively with diluted hydrochloric acid 3 times, sodium hydrogen carbonate solution and brine, and dried over magnesium sulfate and evaporated under reduced pressure to give 5-tert-butylindole (2.10 g).
Workup
- temperatureAfter cooling
- customthe reaction mixture was partitioned between diluted hydrochloric acid and diethyl ether
- washThe ether layer was washed successively with diluted hydrochloric acid 3 times, sodium hydrogen carbonate solution and brine
- dry with materialdried over magnesium sulfate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-834720b5610f4d7e80026ebd87598440
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05994378
Reaction notes
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