p-Toluenesulfonic acid → HCID 86709380, compound

HRID 2172207Notes

Reaction equation

HRID 2172207 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:12])[CH:8]=2)[N:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>ClCCl.O1CCCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][O:13]3)[CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 14798Sodium HydroxideHCID 221325772-Chloroquinolin-6-ol

Product 1

HCID 86709380HCID 86709380, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Chloroquinolin-6-ol (36 g, 0.20 mol) was dissolved in dichloromethane (500 ml) and tetrahydrofuran (500 ml). 3,4-dihydro-2H-pyran (74 ml, 0.81 mol) and p-toluenesulfonic acid (0.49 g, 0.005 mol) were added to the mixture in ice cooling water bath, followed by stirring at room temperature overnight. A 10% sodium hydroxide aqueous solution was added to the reaction mixture, followed by extraction with dichloromethane. The result was dried over potassium carbonate and subjected to filtration, and then the filtrate was concentrated under reduced pressure. The crude crystal thus obtained was recrystallized from ethanol to afford the title compound as a colorless granular compound (47 g, yield 89%).

Workup

  1. temperaturecooling water bath
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe result was dried over potassium carbonate
  4. filtrationsubjected to filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe crude crystal thus obtained
  7. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-8579bf8815ea4891a6e19af5fa57e7cc
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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