7-Nitroindole → 3-Chloro-7-nitroindole

HRID 863436Notes

Reaction equation

HRID 863436 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

7-Nitro-1H-indole (1.076 g, 6.64 mmol) was dissolved in 30 ml of acetonitrile, followed by the addition of 920 mg (6.89 mmol) of N-chlorosuccinimide. The obtained mixture was stirred at room temperature for 36 hours. A saturated aqueous solution of sodium hydrogencarbonate was added to the resulting mixture to form a precipitate. The precipitate was recovered by filtration and washed with water to give 1.2 g of powdery 3-chloro-7-nitro-1H-indole. This powder (863 mg, 4.39 mmol) was suspended in 10 ml of ethanol, followed by the addition of 4.95 g (21.9 mmol) of stannous chloride dihydrate and 100 μl of concentrated hydrochloric acid. The obtained mixture was heated under reflux for 30 minutes, followed by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The obtained mixture was filtered to remove insolubles. Ethyl acetate was added to the filtrate to conduct extraction. The organic phase 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. customto form a precipitate
  2. filtrationThe precipitate was recovered by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-75df171c7bd74032ac3a67e9e4890497
Source dataset
uspto-grants-1998_02
Patent number
US05721246

Reaction notes

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