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

HRID 1167093Notes

Reaction equation

HRID 1167093 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-f593722c3799443888948575a6c706e3
Source dataset
uspto-grants-2003_09
Patent number
US06617317B1

Reaction notes

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