Water → 4-Nitro-1,3-dihydro-2H-indol-2-one

HRID 1275663Notes

Reaction equation

HRID 1275663 reaction equation
P(=O)(O)(O)O.Cl[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:16]([O-:18])=[O:17])[NH:9][CH:8]=1.[OH2:19]>COCCO>[N+:16]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[CH2:7][C:8](=[O:19])[NH:9]2)([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 120498633-CHLORO-4-NITRO-1H-INDOLE

Product 1

HCID 216778744-Nitro-1,3-dihydro-2H-indol-2-one

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
95 °C

Procedure

Phosphoric acid (35 mL of 86%) is added to a solution of 3-chloro-4-nitroindole (1.27 g, 6.46 mmol) in 2-methoxyethanol (50 mL) at 100° C. The resulting brown colored solution is stirred at 95° C. for 3.5 hours. The reaction is cooled to room temperature and then poured into 500 mL of water. The aqueous layer is extracted three times with ethyl acetate. 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 2% methanol/methylene chloride as the eluent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 0.90 g of slightly impure 4-nitrooxindole as an orange solid.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThe aqueous layer is extracted three times with ethyl acetate
  3. dry with materialThe ethyl acetate layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents removed by rotary evaporation
  6. customThe crude material is purified via silica gel column chromatography
  7. additionThe product containing fractions
  8. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-1164e58fe4b44a03800002ee524da014
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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