7-Nitroindole → 3-Chloro-7-nitroindole

HRID 1173099Notes

Reaction equation

HRID 1173099 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[Cl:13]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:13][C:9]1[C:8]2[C:12](=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][CH:7]=2)[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 233967-NitroindoleHCID 31398ChlorosuccinimideHCID 516892Sodium Bicarbonate

Product 1

HCID 116225033-Chloro-7-nitroindoleYield 91.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.076 g (6.64 mmol) of 7-nitro-1H-indole was dissolved in 30 ml of acetonitrile, and 920 mg (6.89 mmol) of N-chlorosuccinimide was added thereto. After stirring at room temperature for 36 hours, an aqueous saturated sodium bicarbonate was added thereto. The precipitates were collected by filtration and washed with water, to give 1.2 g of 3-chloro-7-nitro-1H-indole. 863 mg (4.39 mmol) of the powder was suspended in 10 ml of ethanol, and 4.95 g (21.9 mmol) of stannous chloride.dihydrate and 100 μl of concentrated hydrochloric acid were added thereto. After heating under reflux for 30 minutes, an aqueous saturated sodium bicarbonate was added thereto and the insoluble matters were filtered off. After extracting by adding ethyl acetate thereto, the extract was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography, to give 490 mg of the title compound.

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washwashed with water

Sources & evidence

ORD record
ord-88a4e4400fed4f65ae35daa29f7c960a
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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