74588-91-3

Upstream product

• 4636-16-2 iodoacetophenone 
• 91-56-5 indole-2,3-dione 
• 3486-31-5 isatin sodium salt 
• 70-11-1 α-bromoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 17617-34-4 (2‐aminophenyl)oxoacetic acid sodium salt 

Downstream Products

• 1022-86-2 2-benzoylindole 
• 74588-82-2 2-benzoyl-1H-indole-3-carboxylic acid 
• 1374156-10-1 2-benzoyl-3-hydroxy-4-oxo-1,4-dihydroquinoline 
• 180902-40-3 1-benzyl-2-benzoylindole-3-carboxylic acid 

Relevant academic research and scientific papers

Reaction of isatin with alkylating agents with acidic methylenes

The reaction of isatin (1) with different alkyl halides 2 and alkaline carbonates in aprotic polar solvents leads mainly to N-alkyl derivatives 3. The use of alkylating agents that have acidic methylenes leads to competitive formation of the corresponding epoxide 5. The formation of 5 is favored by low-polarity solvents at low temperatures and strong bases. Epoxides 5c, d obtained using NaEtOH/EtOH at 0-5 °C are transformed into the corresponding 4-quinolinones 6 at higher temperatures. The use of Ag2CO3 allows obtaining compounds 3 as major products, along with varying amounts of labile O-alkyl derivatives 4 and dimerization products.

Simple and efficient microwave assisted N-alkylation of isatin

We present herein the results of microwave promoted N-alkylations of isatin (1) with different alkyl, benzyl and functionalized alkyl halides. Reactions were carried out under different conditions, always employing methodologies compatible with MW assisted chemistry. Generation of isatin anion employing diverse bases and solvents or using the preformed isatin sodium salt was tested. The best results were achieved using K2CO3 or Cs 2CO3 and a few drops of N,N-dimethylformamide or N-methyl-2-pyrrolidinone. These reactions present noteworthy advantages over those carried out employing conventional heating.

Direct N-alkylation of isatin by halomethyl ketones

Solid-phase syntheses are reported for 1-(2-oxoalkyl)indoline-2,3-diones. 2005 Springer Science+Business Media, Inc.

A Simple Synthesis of 2-Acyl Indoles from Isatins

N-Phenacyl- and N-acetonyl-isatins can be prepared and converted by treatment with sodium hydroxide into 2-acyl indoles and/or 2-acyl indole-3-carboxylic acids.