Water → 1-benzyl-5-nitro-2,3-dihydro-1H-indole

HRID 1359141Notes

Reaction equation

HRID 1359141 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH2:13]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH2:7][CH2:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 362195-Nitroindoline

Product 1

HCID 98348711-benzyl-5-nitro-2,3-dihydro-1H-indoleYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under the presence of nitrogen, 5-nitroindolin (50 mg, 0.30 mmol) was dissolved in dimethylformamide (2 ml) at room temperature and benzyl bromide (0.04 ml. 0.34 mmol) and potassium carbonate (0.126 ml, 3.0 equivalent) were added and stirred at room temperature for 48 hours. After completing the reaction, water and ethyl acetate (respectively 5 ml) were added to separate layers, washed with brine, dried over anhydrous magnesium sulfate, and concentrated. Finally, the residue was purified through flash column chromatography (an eluent:ethyl acetate/n-hexane=1/4, v/v). As a result, the present compound (45 mg, productive yield 58%) was obtained.

Workup

  1. additionwere added
  2. customto separate layers
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customFinally, the residue was purified through flash column chromatography (an eluent
  7. customAs a result, the present compound (45 mg, productive yield 58%) was obtained

Sources & evidence

ORD record
ord-d81cab0d5c0c41368ac4d3a883fc75fc
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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