Quinaldic Acid → HCID 4866761, compound

HRID 1578162Notes

Reaction equation

HRID 1578162 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([OH:13])=[O:12]>O=[Pt]=O.C(O)(=O)C>[NH:1]1[CH:10]2[CH:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 1

HCID 7124Quinaldic Acid

Product 1

HCID 4866761HCID 4866761, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of quinoline-2-carboxylic acid (30 g, 0.17 mole), glacial acetic acid (1000 ml), and PtO2 (2.0 g) was subjected to hydrogenation at room temperature for 3 hours using 51.7 psia H2 (theory: 58.7 psia H2). The catalyst was removed by filtration and the filtrate was stripped of solvent under reduced pressure. The residue was dissolved in acetonitrile (300 ml) and the mixture was cooled. The product was collected by filtration and washed with acetonitrile and ether; m.p. 254°-258°; yield: 20 g. The filtrate was diluted with ether, cooled, and the product was collected by filtration. The two products were combined to give 23 g (74%) of decahydroquinoline-2-carboxylic acid.

Workup

  1. customThe catalyst was removed by filtration
  2. dissolutionThe residue was dissolved in acetonitrile (300 ml)
  3. temperaturethe mixture was cooled
  4. filtrationThe product was collected by filtration
  5. washwashed with acetonitrile and ether
  6. additionThe filtrate was diluted with ether
  7. temperaturecooled
  8. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-436bd42c7ab142b18e5852a3e710e72e
Source dataset
uspto-grants-1981_09
Patent number
US04291163

Reaction notes

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