4-tert-Butyl-2,6-dinitrochlorobenzene → 2-Chloro-5-(1,1-dimethylethyl)-3-nitrobenzenamine

HRID 443883Notes

Reaction equation

HRID 443883 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[H][H]>CO>[Cl:1][C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([C:11]([CH3:13])([CH3:12])[CH3:14])=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 2

HCID 751764-tert-Butyl-2,6-dinitrochlorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 205145812-Chloro-5-(1,1-dimethylethyl)-3-nitrobenzenamineYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 100 parts of 2-chloro-5-(1,1-dimethylethyl)-1,3-dinitrobenzene and 800 parts of methanol is hydrogenated at normal pressure and at room temperature with 10 parts of ruthenium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. The residue is purified by column-chromatography over silica gel using trichloromethane as eluent. The pure fractions are collected and the eluent is evaporated, yielding 69 parts (78%) of 2-chloro-5-(1,1-dimethylethyl)-3-nitrobenzenamine as a residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residue is purified by column-chromatography over silica gel
  4. customThe pure fractions are collected
  5. customthe eluent is evaporated

Sources & evidence

ORD record
ord-f3ecb6682af145ea86608b790b7dd8df
Source dataset
uspto-grants-1981_04
Patent number
US04262004

Reaction notes

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