Ethylamine → 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid ethylamide

HRID 49135Notes

Reaction equation

HRID 49135 reaction equation
[CH2:1]([NH2:3])[CH3:2].[C:4]([C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][C:10](=[O:16])[NH:11]2)(O)=[O:5].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH2:1]([NH:3][C:4]([C:7]1[C:8]2[CH2:9][C:10](=[O:16])[NH:11][C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 2724699PyBOPHCID 103973292-oxo-2,3-dihydro-1H-indole-4-carboxylic acid

Product 1

HCID 695865512-oxo-2,3-dihydro-1H-indole-4-carboxylic acid ethylamideYield 65.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Ethylamine (2.1 mL of 2.0M solution in tetrahydrofuran, 4.2 mmol) was added dropwise to a suspension of 4-carboxy-2-oxindole (380 mg, 2.1 mmol) in dimethylformamide (8 mL), followed by 4-dimethylaminopyridine (385 mg, 3.15 mmol) and PyBOP (2.185 g, 4.2 mmol). The mixture was stirred at room temperature for 6 hrs. The reaction was concentrated. The residue was dissolved in dichloromethane, washed with saturated sodium bicarbonate and brine, dried, concentrated and recrystallized to give 280 mg (65%) of 2-oxo-2,3-dihydro-1H-indole-4-carboxylic acid ethylamide.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated sodium bicarbonate and brine
  4. customdried
  5. concentrationconcentrated
  6. customrecrystallized

Sources & evidence

ORD record
ord-f94f15b92d39484a83d8b485378b2aec
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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