Triethylamine → HCID 10541961, compound

HRID 441225Notes

Reaction equation

HRID 441225 reaction equation
[CH3:1][CH:2]1[CH:10]([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(N(CC)CC)C.[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>ClCCl>[CH3:1][CH:2]1[CH:10]([CH3:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:26](=[O:27])[C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 309442,3-Dimethyl-2,3-dihydro-1H-indole

Product 1

HCID 10541961HCID 10541961, compoundYield 5,616.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,3-dimethylindoline (736 mg) and triethylamine (0.836 ml) in dichloromethane (20 ml) was added p-nitrobenzoyl chloride (928 mg) and the solution was stirred at ambient temperature for 4 hours. The solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine, and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was solidified with n-hexane to give 2,3-dimethyl-1-(4-nitrobenzoyl)indoline (83.2 g).

Workup

  1. washThe solution was washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4fcce5b1bc84401698aa70cd8497960e
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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