Dimethyl malonate → 6-Methoxyoxindole

HRID 1728104Notes

Reaction equation

HRID 1728104 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O.C(OC)(=O)[CH2:14][C:15](OC)=[O:16].[H-].[Na+]>[Fe]>[CH3:9][O:8][C:5]1[CH:4]=[C:3]2[C:2]([CH2:14][C:15](=[O:16])[NH:10]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 251404-Chloro-3-nitroanisole

Product 1

HCID 27937496-MethoxyoxindoleYield 18.4%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

In a manner similar to the method described in example 167a, 1-chloro-4-methoxy-2-nitro-benzene (19 g, 0.1 mol) was reacted with dimethyl malonate (16 g, 0.2 mol), NaH and iron power to give 6-methoxy-1,3-dihydro-indol-2-one (3 g, 18%).

Sources & evidence

ORD record
ord-c0c477c2c2964da6a27dd33023cb8694
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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