Ethylene Glycol → HCID 70456308, compound

HRID 1284925Notes

Reaction equation

HRID 1284925 reaction equation
ClC(Cl)C.[CH3:5][N:6]1[CH2:20][CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2=[CH:10][CH:11]=[C:12]3[C:16]([NH:15][C:14](=[O:17])[C:13]3=[O:18])=[C:8]2[CH2:7]1.[CH2:27](O)[CH2:28][OH:29].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[O:17]=[C:14]1[CH:13]2[O:18][CH2:27][CH2:28][O:29][C:11]3=[C:12]2[C:16](=[C:8]2[CH2:7][N:6]([CH3:5])[CH2:20][CH:19]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[C:9]2=[CH:10]3)[NH:15]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 63651,1-DichloroethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 13491592HCID 13491592, compound

Product 1

HCID 70456308HCID 70456308, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of dichloroethane are added to 20.6 g (0.0624 mol) of 8-methyl-6-phenyl-6,7,8,9-tetrahydro-1H-pyrido[4,3-g]indole-2,3-dione, 21 ml (0.374 mol) of ethylene glycol and 0.336 g (0.00176 mol) of toluene-4-sulphonic acid monohydrate, with stirring, and the mixture is heated under reflux for 3.5 hours, using a water separator. Ice is added to the reaction mixture and the mixture is brought to pH 6.8 with aqueous KHCO3 solution. The mixture is extracted with CH2Cl2, the CH2Cl2 phase is washed with H2O and dried over Na2SO4 and the solvent is stripped off in a rotary evaporator. The residue is chromatographed on Al2O3 (aluminum oxide from E. Merck, Darmstadt) using an eluent mixture of ethyl acetate and MeOH (20:0.2). After trituration with ethyl acetate/petroleum ether, the substance becomes crystalline. It is dried over P2O5 at 80° C. in vacuo.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 3.5 hours
  3. additionIce is added to the reaction mixture
  4. extractionThe mixture is extracted with CH2Cl2
  5. washthe CH2Cl2 phase is washed with H2O
  6. dry with materialdried over Na2SO4
  7. customthe solvent is stripped off in a rotary evaporator
  8. customThe residue is chromatographed on Al2O3 (aluminum oxide from E. Merck, Darmstadt)
  9. additionan eluent mixture of ethyl acetate and MeOH (20:0.2)
  10. dry with materialIt is dried over P2O5 at 80° C. in vacuo

Sources & evidence

ORD record
ord-38865ff46e164f72a92c0d16454caa7f
Source dataset
uspto-grants-1986_01
Patent number
US04564613

Reaction notes

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