p-Toluenesulfonic acid → HCID 22037001, compound

HRID 1790002Notes

Reaction equation

HRID 1790002 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2C=O)[CH:4]=[CH:3][CH:2]=1.C(O[CH:16]([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])C.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:21]([O:20][CH:16]([O:17][CH2:18][CH3:19])[C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[N:1]=[CH:2][CH:3]=[CH:4]2)[CH3:22]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 31214Ethyl orthoformateHCID 1701038-Quinolinecarboxaldehyde

Product 1

HCID 22037001HCID 22037001, compoundYield 84.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 8-quinolinecarboxaldehyde (0.248 mol), triethoxymethane (0.4464 mol) and 4-methylbenzenesulfonic acid (4 g) in ethanol (250 ml) was stirred and refluxed for 1 hour, brought to room temperature, poured out into K2CO3 10% and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The product was used without further purification, yielding 48.5 g (80%) of 8-(diethoxymethyl)-quinoline (interm. 29).

Workup

  1. temperaturerefluxed for 1 hour
  2. custombrought to room temperature
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe product was used without further purification

Sources & evidence

ORD record
ord-9ca8affbf2c845d8a5ea54ffd2219358
Source dataset
uspto-grants-2006_07
Patent number
US07071192B1

Reaction notes

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