Hydrochloric Acid → 1,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

HRID 1462900Notes

Reaction equation

HRID 1462900 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].[ClH:14]>O=[Pt]=O.C(O)(=O)C>[ClH:14].[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7124Quinaldic Acid

Product 1

HCID 457901311,2,3,4-Tetrahydroquinoline-2-carboxylic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

2-Quinolinecarboxylic acid (30 g), glacial acetic acid (500 ml), and PtO2 (0.9 g) were combined and hydrogenated at 50°-58° for 45 minutes. After cooling to room temperature, concentrated hydrochloric acid (35 ml) was added, the catalyst was filtered, and the filtrate evaporated in vacuo. The residue was dissolved in acetonitrile (200 ml) and the solution cooled overnight. The resulting product was filtered; yield 25 g, m.p. 122°-125°.

Workup

  1. filtrationthe catalyst was filtered
  2. customthe filtrate evaporated in vacuo
  3. dissolutionThe residue was dissolved in acetonitrile (200 ml)
  4. temperaturethe solution cooled overnight
  5. filtrationThe resulting product was filtered

Sources & evidence

ORD record
ord-0c43f30324614f7da6ea8e5c8dfaadf9
Source dataset
uspto-grants-1984_07
Patent number
US04461896

Reaction notes

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