Decalin → HCID 22922504, compound

HRID 1081474Notes

Reaction equation

HRID 1081474 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([N+:11]([O-])=O)[CH:3]=1.[CH:14]([C:17]1[CH:23]=[CH:22][C:20](N)=[CH:19][CH:18]=1)([CH3:16])[CH3:15].C1C2C(CCCC2)CCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([NH:11][C:20]2[CH:22]=[CH:23][C:17]([CH:14]([CH3:16])[CH3:15])=[CH:18][CH:19]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 7044DecalinHCID 74644-IsopropylanilineHCID 330974-Chloro-1,2-dinitrobenzene

Product 1

HCID 22922504HCID 22922504, compoundYield 60.5%

Procedure

A mixture of 15 g of 4-chloro-1,2-dinitrobenzene, 10 g of 4-isopropylaniline and 25 ml of Decaline® is refluxed for 15 hours. The reaction mixture is concentrated under 0.01 mm Hg, the residue is taken up with water, extracted with ether, washed with a 1N solution of HCl and with water and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using iso ether as the eluent to give 13 g of the expected product, which is used as such in the next step.

Workup

  1. temperatureis refluxed for 15 hours
  2. concentrationThe reaction mixture is concentrated under 0.01 mm Hg
  3. extractionextracted with ether
  4. washwashed with a 1N solution of HCl and with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent is evaporated off under vacuum
  7. customThe residue is chromatographed on silica using iso ether as the eluent

Sources & evidence

ORD record
ord-f291f411cf0f4cd7ab32af869460ca35
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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