HCID 178469285, compound → HCID 178469294, compound

HRID 2409509Notes

Reaction equation

HRID 2409509 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1>Cl.[Pt](=O)=O>[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1

Participants

4

Reactant 1

HCID 178469285HCID 178469285, compound

Product 1

HCID 178469294HCID 178469294, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of ethyl 4-hydroxy-2-quinolinecarboxylate (2.18 g, 10.0 mmol) in 80 mL of concentrated hydrochloric acid was added platinum (IV) oxide. The mixture was subjected to hydrogenation in a Parr shaker apparatus under 50 lbs of H2 for 72 h. The reaction was filtered and concentrated in vacuo to provide ethyl 4-hydroxy-5,6,7,8-tetrahydroquinoline-2-carboxylate that gave a mass ion (ES+) of 222.0 for [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-710265ae95324ff7973eb3aa8678157e
Source dataset
uspto-grants-2014_08
Patent number
US08815902B2

Reaction notes

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