Isopropylamine → HCID 86735858, compound

HRID 848660Notes

Reaction equation

HRID 848660 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH:11]([CH3:13])[CH3:12])[C:5]([CH3:14])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[CH:18]([NH2:21])([CH3:20])[CH3:19]>C1(C)C=CC=CC=1>[CH:18]([NH:21][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([CH:11]([CH3:13])[CH3:12])[C:5]([CH3:14])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 86735859HCID 86735859, compound

Product 1

HCID 86735858HCID 86735858, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-4,6-dinitro-o-cymene (4.0 g, 0.0155 mole) and isopropylamine (3.2 g, 0.054 mole) in toluene is heated in a bomb at 100° C. for 4 hours. The cooled mixture is washed with aqueous bicarbonate solution, dried over magnesium sulfate, and concentrated to leave the crude product which is purified by dry column chromatography to yield 3.2 g of product with mp 54°-55° C. By using one of the aforementioned procedures for the dinitration of the appropriate N-alkyl-4-alkyl-m-toluidines or by reacting the appropriate amine with the desired 3-chloro-2,4-dinitro-6-alkyltoluene the following compounds are prepared.

Workup

  1. washThe cooled mixture is washed with aqueous bicarbonate solution
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customto leave the crude product which
  5. customis purified
  6. customby dry column chromatography

Sources & evidence

ORD record
ord-80d8cad988a64008b0059775a07d69a2
Source dataset
uspto-grants-1981_10
Patent number
US04297127

Reaction notes

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