Anthracene-9-carbonyl chloride → N-cyclohexylmethyl-N-propargyl-9-anthramide

HRID 372096

Reaction equation

HRID 372096 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15](Cl)=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:18]([NH:21][CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:19]#[CH:20].[O-2].[Mg+2]>O1CCCC1>[CH:23]1([CH2:22][N:21]([CH2:18][C:19]#[CH:20])[C:15]([C:13]2[C:14]3[C:5]([CH:6]=[C:7]4[C:12]=2[CH:11]=[CH:10][CH:9]=[CH:8]4)=[CH:4][CH:3]=[CH:2][CH:1]=3)=[O:16])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 167528Anthracene-9-carbonyl chlorideHCID 6850729Magnesium monoxideHCID 20353285(Cyclohexylmethyl)(prop-2-yn-1-yl)amine

Product 1

HCID 20353277N-cyclohexylmethyl-N-propargyl-9-anthramideYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 12.66 g of 9-anthroyl chloride in 50 ml of tetrahydrofuran is added dropwise to a stirred mixture of 8.69 g of N-propargylcyclohexylmethylamine and 9 g of magnesium oxide in 80 ml of tetrahydrofuran. After stirring at room temperature overnight, the mixture is filtered and the filtrate is concentrated to dryness. The residue is taken up in methylene chloride and washed, in turn, with dilute sulfuric acid, water, and dilute sodium hydroxide solution, and dried. Removal of the solvent gives 14.7 g of N-cyclohexylmethyl-N-propargyl-9-anthramide as an oil. It is dissolved in 100 ml of p-xylene and the mixture is heated under reflux for three hours. The solvent is removed, and the residue is heated under reflux with 60 ml of tetrahydrofuran and 60 ml of 15% aqueous sodium hydroxide solution for one hour. The mixture is concentrated to a small volume, diluted with water and filtered. The solid is washed with dilute alkali and water, dried, and crystallized from toluene to give 6.68 g of 2-cyclohexylmethyl-3,5-dihydro-5,9b-o-benzenobenz[e]isoindol-1(2H)-one; nmr spectrum: τ 2.3-3.4 (m, 9); 4.8 (d, J = 6Hz, 1) 5.9 (d, J = 2Hz, 2); 6.6 (d, J = 6.5 Hz, 2) and 8.0-9.2 (m, 11).

Workup

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. washwashed, in turn, with dilute sulfuric acid, water, and dilute sodium hydroxide solution
  4. customdried
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-26d5101c5bf44a2ca1c1bc500fd6ac5a
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Linked notes

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