Hydrochloric Acid → 4-Methoxy-N-methyl-2-nitrobenzenamine

HRID 1419120Notes

Reaction equation

HRID 1419120 reaction equation
C(O[C:6]([N:8](C)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18])=O)(C)(C)C.Cl>O1CCOCC1>[CH3:6][NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[N+:17]([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 53900404tert-butyl N-(4-methoxy-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 35543134-Methoxy-N-methyl-2-nitrobenzenamineYield 90.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A procedure similar to that described in Preparation 8 was repeated, except that 2.0 g of N-t-butoxycarbonyl-N-methyl-4-methoxy-2-nitroaniline (prepared as described in Preparation 23) and 30 ml of a 4N solution of hydrogen chloride in 1,4-dioxane were used, to give 1.17 g of the title compound having an Rf value=0.62 (on thin layer chromatography on silica gel; developing solvent: a 1:5 by volume mixture of ethyl acetate and hexane).

Workup

  1. customA procedure similar to that described in Preparation 8

Sources & evidence

ORD record
ord-d6fe830b6cb54433860642699266d1f2
Source dataset
uspto-grants-1999_03
Patent number
US05886014

Reaction notes

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