Acetic Anhydride → 1-Acetyl-6-(methylthio)-benz[cd]indol-2-(1H)-one
Reaction equation
[CH3:1][S:2][C:3]1[C:4]2[C:5]3[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]=3[CH:13]=[CH:14][CH:15]=2.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([N:8]1[C:9]2[C:5]3[C:4](=[CH:15][CH:14]=[CH:13][C:6]=3[C:7]1=[O:12])[C:3]([S:2][CH3:1])=[CH:11][CH:10]=2)(=[O:18])[CH3:17]Participants
3
Procedure
A mixture of 1 g of 6-(methylthio)-benz[cd]-indol-2(1H)-one (Example 2) and 10 ml of acetic anhydride is stirred and heated at reflux for 2 hours, cooled and filtered. The cake is washed with ethanol and ether then dried. The dried cake is suspended in 15 ml of hot ethanol, filtered and the cake crystallized from 150 ml of ethanol to afford the desired product as a solid.
Workup
- temperatureheated
- temperatureat reflux for 2 hours
- temperaturecooled
- filtrationfiltered
- washThe cake is washed with ethanol and ether
- customthen dried
- filtrationfiltered
- customthe cake crystallized from 150 ml of ethanol
Sources & evidence
- ORD record
- ord-baf31a8f9aaf4b7d937c1479ff9364c5
- Source dataset
- uspto-grants-1993_07
- Patent number
- US05229411
Reaction notes
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