8-Hydroxyquinoline → HCID 85777814, compound

HRID 408964Notes

Reaction equation

HRID 408964 reaction equation
[P:1]([Cl:5])(Cl)([Cl:3])=[O:2].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[OH:16])[CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>C(OCC)C>[P:1]([Cl:5])([Cl:3])(=[O:2])[O:16][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[N:6]=[CH:7][CH:8]=[CH:9]2

Participants

5

Reactant 3

HCID 19238-HydroxyquinolineHCID 8471TriethylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 85777814HCID 85777814, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Phosphorus oxychloride (0.58 mL, 1 equiv) and quinolin-8-ol (Aldrich, 900 mg, 1 equiv) were stirred in anhydrous diethyl ether (25 mL). Anhydrous triethylamine was added (0.86 mL, 1 equiv) at −78° C. and the solution was allowed to warm to room temperature after 25 min. The triethylamine hydrochloride salt was filtered off and the solvent was removed under reduced pressure to give a clear pale yellow syrup (870 mg, 54%). This crude product was used for next step directly.

Workup

  1. filtrationThe triethylamine hydrochloride salt was filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9629f86c3f2449e1ae91e2323d592a55
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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