Hydrogen Peroxide → 2-Amino-4,6-dimethoxybenzamide

HRID 526667Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:4]=1[C:5](=[O:15])C(=O)[NH:7]2.[OH-].[Na+].OO.CC[N:22]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>>[NH2:7][C:8]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([NH2:22])=[O:15]

Participants

Reactant 4

HCID 784Hydrogen Peroxide

HCID 14798Sodium Hydroxide

HCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

HCID 18410139Edci hobt

Product 1

HCID 203490162-Amino-4,6-dimethoxybenzamide

Procedure

2-Amino-4,6-dimethoxybenzamide has been prepared from 4,6-dimethoxyisatoic anhydride. The 4,6-dimethoxyisatoic anhydride was, in turn, prepared by a reaction of 4,6-dimethoxyanthranilic acid with phosgene (U.S. Pat. No. 4,191,840 and Org. Synth. 1947, 27, 45). A different route converts 3,5-dimethoxyaniline to its hydrochloride salt, after which the salt is reacted with oxalyl chloride to give 4,6-dimethoxyisatin. The isatin is converted to the target compound via an unstable carboxyl intermediate by reaction with sodium hydroxide and hydrogen peroxide followed by an EDCI/HOBt-mediated coupling to produce 2-amino-4,6-dimethoxybenzamide (WO 2008/92231).

Sources & evidence

ORD record: ord-4b93e81b9d54413289b26af45a66819b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346743B2

Reaction notes

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