Methanol → N-Methyloxindole

HRID 2200164Notes

Reaction equation

HRID 2200164 reaction equation
N(C([O:10][CH2:11][CH3:12])=O)=NC(OCC)=O.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)C[C:14]1=O.CO.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:14][N:13]1[C:21]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][C:11]1=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 321710Oxindole

Product 1

HCID 6096N-MethyloxindoleYield 59.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add diethyl azodicarboxylate (DEAD, 8.0 g, 44.9 mmol) dropwise to a solution of indolin-2-one (4.0 g, 30.0 mmol), methanol (1.4 g, 44.9 mmol) and triphenylphosphine (12.0 g, 44.9 mmol) in THF (40 mL) at 0° C., stir the reaction at room temperature overnight. Concentrate under reduced pressure, purify the resulting residue with flash chromatography (silica gel, EtOAc:PE=1:3) to afford the title compound (2.6 g, 59.1%). MS: (M+1): 148.2.

Workup

  1. customthe reaction at room temperature overnight
  2. concentrationConcentrate under reduced pressure
  3. custompurify the resulting residue with flash chromatography (silica gel, EtOAc:PE=1:3)

Sources & evidence

ORD record
ord-2fff88bea1e1482799f59ccf12c126ba
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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