Isopropylamine → HCID 86735858, compound

HRID 261292Notes

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

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. ##STR41##Ex. No. R1 R2 Y MP° C.______________________________________201 H C3H7 -i C2H5 46°-46.5°202 H C4H9 -sec " 37.5°-38°203 H CH(C2H5)2 " 51°-53°204 H C3H7 -i C3H7 -n 55°205 H CH(C2H5)2 " orange oil206 H C3H7 -i C3H7 -i 54°-55°207 H C3H7 -n " orange-red oil208 H C4H9 -sec " orange oil209 H CH(C2H5)2 " red oil210 H CH(C2H5)2 C4H9 -n 47.5°-50°211 H CH(C2H5)2 C 4 H9 -sec orange oil______________________________________

Workup

washThe cooled mixture is washed with aqueous bicarbonate solution
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto leave the crude product which
customis purified
customby dry column chromatography

Sources & evidence

ORD record: ord-79905b06f5c74872b2a48c640ab4ce0a
Source dataset: uspto-grants-1979_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04165231

Reaction notes

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