Water → 1,2,3,4-Tetrahydro-2-oxo-7-quinolinecarboxaldehyde

HRID 1256277Notes

Reaction equation

HRID 1256277 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([C:12]#N)=[CH:7][CH:8]=2)[NH:3]1.[OH2:14]>C(O)=O.[Ni]>[O:1]=[C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]=[O:14])=[CH:7][CH:8]=2)[NH:3]1

Participants

5

Reactant 2

HCID 962WaterHCID 586868452-Oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile

Product 1

HCID 593980391,2,3,4-Tetrahydro-2-oxo-7-quinolinecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 284Formic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Step R1-3: To a suspension of 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbonitrile (160 g) in HCO2H (1.6 L) was added Raney Nickel Catalyst (slurry in water, 160 g) at room temperature over 30 minutes. The mixture was heated at 100° C. for 2 hours. After cooling to room temperature, the reaction mixture was filtrated through a pad of Celite and washed with HCO2H. The filtrate was concentrated to obtain a solid. The solid was stirred with water (1.3 L) and filtrated to obtain 2-oxo-1,2,3,4-tetrahydroquinoline-7-carbaldehyde as a pale brown solid (156 g).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtrated through a pad of Celite
  3. washwashed with HCO2H
  4. concentrationThe filtrate was concentrated
  5. customto obtain a solid
  6. filtrationfiltrated

Sources & evidence

ORD record
ord-55df51ce31094e379a5c0a29173b3b6c
Source dataset
uspto-grants-2013_06
Patent number
US08461182B2

Reaction notes

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