8-Hydroxy-5,6,7,8-tetrahydroquinoline → 6,7-Dihydro-5H-quinoline-8-one

HRID 720745Notes

Reaction equation

HRID 720745 reaction equation
[OH:1][CH:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:5][CH2:4][CH2:3]1>C(Cl)Cl.O=[Mn]=O>[N:10]1[C:11]2[C:2](=[O:1])[CH2:3][CH2:4][CH2:5][C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 118159398-Hydroxy-5,6,7,8-tetrahydroquinoline

Product 1

HCID 117447776,7-Dihydro-5H-quinoline-8-oneYield 82%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 8-hydroxy-5,6,7,8-tetrahydroquinoline (13.96 g, 93.6 mmol) in dry CH2Cl2 (400 mL) was added solid <5 micron activated 85% MnO2 (manganese IV oxide) (82.22 g, 804 mmol). The resulting black suspension was stirred 18 h, at which point the mixture was filtered through a cake of celite and washed with CH2Cl2 (3×50 mL). The combined washings were concentrated to provide 11.27 g (82%) of the title compound as a pale yellow solid, which was used in subsequent reactions without further purification. This material displayed spectra identical to those reported above.

Workup

  1. filtrationwas filtered through a cake of celite
  2. washwashed with CH2Cl2 (3×50 mL)
  3. concentrationThe combined washings were concentrated

Sources & evidence

ORD record
ord-06d91f44208247af8f4ce952523d8d31
Source dataset
uspto-grants-2006_11
Patent number
US07135570B2

Reaction notes

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