Hydrochloric Acid → Acenaphtho[1,2-b]quinoline-10-methanol

HRID 1073633Notes

Reaction equation

HRID 1073633 reaction equation
[CH:1]1[CH:10]=[CH:9][C:8]2[C:3]3=[C:4]([C:11]4[C:20]([C:2]=13)=[CH:19][C:18]1[CH:17]=[C:16]([C:21](OCC)=[O:22])[CH:15]=[CH:14][C:13]=1[N:12]=4)[CH:5]=[CH:6][CH:7]=2.C1COCC1.Cl>O>[CH:1]1[CH:10]=[CH:9][C:8]2[C:3]3=[C:4]([C:11]4[C:20]([C:2]=13)=[CH:19][C:18]1[CH:17]=[C:16]([CH2:21][OH:22])[CH:15]=[CH:14][C:13]=1[N:12]=4)[CH:5]=[CH:6][CH:7]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13358871Ethyl acenaphtho[1,2-b]quinoline-10-carboxylate

Product 1

HCID 14555906Acenaphtho[1,2-b]quinoline-10-methanolYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a RB flask equipped with magnetic stirring bar, reflux condenser, N2 inlet line with bubbler was added ethyl acenaphtho[1,2-b]quinoline-10-carboxylate (H. G. Pars Pharmaceutical Laboratories, Inc., 6.75 g, 23 mmol and dry THF (400 mL). The mixture was stirred at reflux for 3 h and then poured into H2O (1 L). The reaction mixture was acidified with 1N HCl and the resulting white solid was filtered, washed with additional H2O (500 mL) then dissolved in CH2Cl2 (500 mL), dried (Na2SO4), filtered, passed through a small plug of SiO2 using CH2Cl2 as the eluting solvent. The appropriate fractions were combined and the volume reduced to 100 mL and diluted to 400 mL with hexane. The resulting material was filtered, washed with hexane (100 mL) and placed in a vacuum oven overnight. A total of 5.52 g (81.6% yield) of acenaphtho[1,2-b]quinoline-10-methanol, mp 215°-218° was obtained which analyzed correctly (C,H,N) for the assigned structure.

Workup

  1. customTo a RB flask equipped with magnetic stirring bar
  2. temperaturereflux condenser, N2 inlet line with bubbler
  3. temperatureat reflux for 3 h
  4. filtrationthe resulting white solid was filtered
  5. washwashed with additional H2O (500 mL)
  6. dissolutionthen dissolved in CH2Cl2 (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. additiondiluted to 400 mL with hexane
  10. filtrationThe resulting material was filtered
  11. washwashed with hexane (100 mL)
  12. customplaced in a vacuum oven overnight

Sources & evidence

ORD record
ord-6355a643434c40d499ba7c2859bcbba2
Source dataset
uspto-grants-1990_11
Patent number
US04970227

Reaction notes

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