N,N-Diethylethanamine trihydrofluoride → 8-Hydroxyquinoline

HRID 1260126Notes

Reaction equation

HRID 1260126 reaction equation
C(C1C=CC([C:11]2[CH:20]=[CH:19][C:18]([O:21][Si](C(C)(C)C)(C)C)=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](C)=[N:16]3)=CC=1)(C)(C)C.F.F.F.C(N(CC)CC)C>C1COCC1>[OH:21][C:18]1[CH:19]=[CH:20][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2

Participants

4

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 68651970HCID 68651970, compound

Product 1

HCID 19238-HydroxyquinolineYield 180.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 300 mL flask was added 6.7 g of 5-(4-t-butyl-phenyl)-2-methyl-8-t-butyldimethylsiloxyquinoline and 100 ml dry THF. The mixture was stirred under nitrogen while 13.5 ml triethylamine trihydrofluoride (Aldrich) was added in 5 portions over 30 min. The reaction mixture was stirred at room temperature for 2 h and the solvents removed in vacuo. The resulting oil was purified by silica chromatography, first eluting with 15% dichloromethane in hexanes and then collecting the product by elution with 50% dichloromethane in hexanes to give 4.33 g of the desired product quinaldine 2a as a colorless solid.

Workup

  1. additionwas added in 5 portions over 30 min
  2. customthe solvents removed in vacuo
  3. customThe resulting oil was purified by silica chromatography
  4. washfirst eluting with 15% dichloromethane in hexanes
  5. customcollecting the product
  6. washby elution with 50% dichloromethane in hexanes

Sources & evidence

ORD record
ord-9c843249ef3f4976accc597d4eacf014
Source dataset
uspto-grants-2013_06
Patent number
US08470208B2

Reaction notes

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