Triethylamine → 1-Methyl-5-nitroindolin-2-one

HRID 1887715Notes

Reaction equation

HRID 1887715 reaction equation
Cl[CH2:2][C:3]([N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:4].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:15][N:5]1[C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[CH2:2][C:3]1=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 114361292-Chloro-N-methyl-N-(4-nitro-phenyl)-acetamide

Product 1

HCID 27279611-Methyl-5-nitroindolin-2-one

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 2-Chloro-N-methyl-N-(4-nitrophenyl)acetamide (100 mg, 0.44 mmol), Pd2(dba)3 (20 mg, 0.022 mmol), 2-(di-tert-butylphosphino)biphenyl (13 mg, 0.044 mmol) and triethylamine (91 μl, 0.66 mmol) in toluene was heated at 80° C. for 3 h. The reaction was 78% complete by NMR.

Sources & evidence

ORD record
ord-534ba9b39bb1409e9030f1b03df5d556
Source dataset
uspto-grants-2013_08
Patent number
US08501763B2

Reaction notes

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