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

HRID 389053Notes

Reaction equation

HRID 389053 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-a5948c04f2634bba8134fc72157cdf78
Source dataset
uspto-grants-2013_02
Patent number
US08378099B2

Reaction notes

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