5-Chloro-2,3,3-trimethyl-3H-indole

General procedure: Heterocyclic phenylhydrazine hydrochloride (1 g) was addedto a 10-mL microwave vessel equipped with a micro magnetic stir bar along with 3-methyl-2-butanone (1.2 mol eq.). Deionized water (3 mL) and sulfuric acid (0.1 mol eq.) was added to the reaction mixture. The reaction vessel was securely capped and then subjected to microwave irradiation for 10 min at 100 °C allowing for the complete transformation of the starting material. The water was decanted off and a saturated solution of sodium bicarbonate (3 mL) was added. The flask was sonicated for 10 min to quench the reactive acid. The liquid was poured off and the resulting oil was dissolved in minimum dichloromethane dried over sodium sulfate for 30 min, gravity filtered and concentrated to yield the corresponding products in quantitative yield.General procedure: Heterocyclic phenylhydrazine hydrochloride (1g) was added to a 10-mL microwave vessel equipped with a micro magnetic stir bar along with 3-methyl-2-butanone (1.2 mol eq.). Deionized water (3mL) and sulfuric acid (0.1 mol eq.) was added to the reaction mixture. The reaction vessel was securely capped and then subjected to microwave irradiation for 10min at 100°C allowing for the complete transformation of the starting material. The water was decanted off and a saturated solution of sodium bicarbonate (3mL) was added. The flask was sonicated for 10 min to quench the reactive acid. The liquid was poured off and the resulting oil was dissolved in minimum dichloromethane dried over sodium sulfate for 30 min, gravity filtered and concentrated to yield the corresponding products in quantitative yield.4-CHLOROPHENYLHYDRAZINE. HCI (5.4g), 3-METHYL-2-BUTANONE (6. 4ml) and acetic acid (70ML) were mixed and heated to 80°C initially, to give a solution. The temperature was then raised to 120°C over 2hrs, during which time a solid separated. TLC ANALYSIS (RPC18. Water/MeCN/TFA) indicated consumption of the hydrazine starting material and generation of a single main product. After evaporation of the solvent under vacuum, the residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic phase was collected, dried (MGS04), filtered and the solvent evaporated to give the crude indolenine. Purification by flash chromatography (SILICA. ETHYL ACETATE/HEXANE) gave 4.66g (80percent) of pure product. MS (MALDI-TOF) M+ 193, 195. 1H-NMR (CDC13) 8 1.30 (6H, s), 2.27 (3H, s), 7.23-7. 29 (2H, m) and 7.44 (1 H, d).

Molecular Weight:193.67
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Exact Mass:193.0658271
Monoisotopic Mass:193.0658271
Topological Polar Surface Area:12.4
Heavy Atom Count:13
Complexity:245
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes