Stannous chloride dihydrate → Ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate

HRID 565061Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[C:7]2[C:3]=1[CH:4]=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:6]2[CH3:21].O.O.[Sn](Cl)Cl.O.N>C(O)C>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:8]2[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]3[C:7]=2[N:6]([CH3:21])[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:4]3)=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 4.10 g (10.9 mmol) of ethyl 4-chloro-1-methyl-7-(4-nitrophenoxy)-2-indolecarboxylate, 12.34 g (54.7 mmol) of tin (II) chloride dihydrate and 150 ml of ethanol was stirred at 70° C. for 3 hours. After the reaction mixture was cooled to room temperature, 28% ammonia water was added to render alkaline and the mixture was extracted with ethyl acetate. Insoluble matters were filtered off. The filtrate was washed with 5% sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 2.70 g of ethyl 7-(4-aminophenoxy)-4-chloro-1-methyl-2-indolecarboxylate.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
extractionthe mixture was extracted with ethyl acetate
filtrationInsoluble matters were filtered off
washThe filtrate was washed with 5% sodium chloride aqueous solution
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-e8598d7f8f0a453aae2910b5a19101a7
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06169107A

Reaction notes

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