2-Bromo-4-methylanisole → 3-hydroxy-3-(2-methoxy-5-methylphenyl)-5-nitro-1,3-dihydro-2H-indol-2-one

HRID 1662709Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[N+:11]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:23])[C:17]2=[O:24])([O-:13])=[O:12]>>[OH:24][C:17]1([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=2[O:9][CH3:10])[C:16]2[C:20](=[CH:21][CH:22]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)[NH:19][C:18]1=[O:23]

Participants

Reactant 2

HCID 891432-Bromo-4-methylanisole

HCID 46692505-Nitroisatin

Product 1

HCID 674299383-hydroxy-3-(2-methoxy-5-methylphenyl)-5-nitro-1,3-dihydro-2H-indol-2-oneYield 95.8%

Procedure

With 10.0 g of 2-bromo-4-methyl anisole and 6.00 g of 5-nitroisatin as starting materials, 9.40 g of the title compound (brown solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record: ord-ef38210aac5f45438c2f6f11af7b4789
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

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