Acetonitrile → 3-CHLORO-4-NITRO-1H-INDOLE

HRID 1275662Notes

Reaction equation

HRID 1275662 reaction equation
[Cl:1]N1C(=O)CCC1=O.[N+:9]([C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][NH:16]2)([O-:11])=[O:10].C(#N)C>C(Cl)Cl>[Cl:1][C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[CH:20][C:12]=2[N+:9]([O-:11])=[O:10])[NH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 31398ChlorosuccinimideHCID 1457664-Nitro-1H-indole

Product 1

HCID 120498633-CHLORO-4-NITRO-1H-INDOLEYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (1.23 g, 9.25 mmol) is added to a solution of 4-nitroindole (1.5 g, 9.25 mmol, Aldrich) in methylene chloride (75 mL). The resulting mixture is heated to reflux for 16 hours. Acetonitrile (10 mL) is added to the mixture and heating is continued for another 16 hours. The reaction is cooled to room temperature and the methylene chloride is removed by rotary evaporation. The residue is taken up in ethyl acetate and washed with water. The ethyl acetate layer is dried over magnesium sulfate, filtered and the solvents removed by rotary evaporation. The crude material is purified via silica gel column chromatography using 30% ethyl acetate/hexane as the eluent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 1.35 g of 3-chloro-4-nitroindole as an orange solid (74%).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 16 hours
  3. temperatureheating
  4. customthe methylene chloride is removed by rotary evaporation
  5. washwashed with water
  6. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvents removed by rotary evaporation
  9. customThe crude material is purified via silica gel column chromatography
  10. additionThe product containing fractions
  11. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-9ccf32803df1478f9504bbb03b629175
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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