Isoquinoline-1-carboxylic acid → 1,2,3,4-Tetrahydroisoquinoline carboxylic acid

HRID 1266553Notes

Reaction equation

HRID 1266553 reaction equation
[C:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1>C(O)(=O)C.O=[Pt]=O>[CH:1]1([C:11]([OH:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

4

Reactant 1

HCID 68092Isoquinoline-1-carboxylic acid

Product 1

HCID 1891121,2,3,4-Tetrahydroisoquinoline carboxylic acidYield 45.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 1-isoquinolinecarboxylic acid (1.67 g) in glacial acetic acid (25 mL) was hydrogenated at 60 p.s.i. over PtO2 (270 mg). When the reaction was complete, the mixture was filtered through diatomaceous earth (Celite), washing the solid pad with MeOH, and the filtrate was concentrated to dryness. The resultant white solid was triturated with cold water and filtered to provide the title compound (775 mg).

Workup

  1. filtrationthe mixture was filtered through diatomaceous earth (Celite)
  2. washwashing the solid pad with MeOH
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe resultant white solid was triturated with cold water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d0db39f5ec3b4181a582c469d728ea8f
Source dataset
uspto-grants-2003_04
Patent number
US06548668B2

Reaction notes

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