2-Nitroaniline → 4-Tert-octyl-2-nitroaniline

HRID 231635

Reaction equation

[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH3:11][C:12]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH2:13]>[Cl-].[Zn+2].[Cl-]>[C:12]([C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=1)([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:11]

Participants

Conditions

Temperature: 60 °C

Procedure

In a 2-liter reaction flask fitted with a condenser, nitrogen inlet, stirrer, thermometer and addition funnel is placed 272 grams (2.0 moles) of anhydrous zinc chloride. The flask is placed under a nitrogen atmosphere and 166 ml (2.0 moles) of concentrated (12N) hydrochloric acid is added over a 10-minute period with the temperature rising from 22° to 40° C. To this is then added 276 grams (2.0 moles) of o-nitroaniline over a 15-minute period to avoid the formation of lumps. The resulting thick red slurry is heated to 60° C. and then 474 grams (3.0 moles) of diisobutylene is added gradually over a 110-minute period with the temperature rising during this period from 60° to 90° C. The deep red fluid reaction mixture is heated for another 18 hours at reflux till only a trace of o-nitroaniline is observed by thin layer chromatography.

Workup

customIn a 2-liter reaction flask
customfitted with a condenser, nitrogen inlet, stirrer
additionthermometer and addition funnel
concentration166 ml (2.0 moles) of concentrated (12N) hydrochloric acid
additionis added over a 10-minute period with the temperature
customrising from 22° to 40° C
waitrising during this period from 60° to 90° C
customThe deep red fluid reaction mixture
temperatureis heated for another 18 hours

Sources & evidence

ORD record: ord-7766e2995dfc4649b0ee45e4ed5658cc
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04847367

Linked notes

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