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

HRID 1655443Notes

Reaction equation

HRID 1655443 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.[H][H]>C(O)(=O)C.[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

5

Reactant 2

HCID 68092Isoquinoline-1-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 1891121,2,3,4-Tetrahydroisoquinoline carboxylic acidYield 63%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of isoquinoline-1-carboxylic acid (12.5 g, 0.072 mole) in 185 ml of glacial acetic acid was hydrogenated at room temperature for 24 hours over 2 g of platinum oxide catalyst under 60 psi hydrogen pressure in a Parr hydrogenation apparatus. The reaction mixture was filteed through a filter pad (celite) and the filtrate evaporated to dryness in vacuo. The solid residue of product was triturated with water, filtered and dried to give 8 g (63% yield) of pure 1.

Workup

  1. customthe filtrate evaporated to dryness in vacuo
  2. customThe solid residue of product was triturated with water
  3. filtrationfiltered
  4. customdried
  5. customto give 8 g (63% yield) of pure 1

Sources & evidence

ORD record
ord-8f1c460397404ee09eeda719e398a4a0
Source dataset
uspto-grants-1993_10
Patent number
US05250660

Reaction notes

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