Triethylamine → N-ethoxalylindoline

HRID 52459

Reaction equation

HRID 52459 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:17](Cl)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>ClCCl.[Cl-].[Na+].O>[C:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1)([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10328IndolineHCID 20884Ethoxalyl chloride

Product 1

HCID 1581489N-ethoxalylindolineYield 108.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of indoline (2.0 g, 16.8 mmol) and triethylamine (5 mL) in dichloromethane (30 mL) was added slowly ethyl chlorooxalate (2.3 mL, 20.1 mmol) at 0° C. The mixture was stirred for 10 min at 0° C. and then for 1 h at room temperature. Brine was added and organic layer was separated. The organic layer was washed with diluted aqueous hydrochloric acid and successively brine, dried over magnesium sulfate, and concentrated to give 4.0 g of N-ethoxalylindoline (100%): 1H NMR (270 MHz, CDCl3) δ8.18 (dd, 1H, J=8, 1 Hz), 7.22 (m, 2H), 7.10 (dd, 1H, J=8, 1 Hz), 4.38 (q, 2H, J=7 Hz), 4.22 (t, 2H, J=8 Hz), 3.20 (t, 2H, J=8 Hz), 1.40 (t, 3H, J=7 Hz).

Workup

  1. waitfor 1 h at room temperature
  2. customorganic layer was separated
  3. washThe organic layer was washed with diluted aqueous hydrochloric acid and successively brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7502193e0e7e4d59a65bd231224295fd
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Linked notes

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