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

HRID 1655442Notes

Reaction equation

HRID 1655442 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

To a solution of isoquinoline-1-carboxylic acid (12.5, 0.072 mole) in 185 ml of glacial acetic acid was added 2 g of platinum oxide and the suspension was hydrogenated at room temperature under 60 psi hydrogen pressure in a Parr hydrogenation apparatus for 24 h. The reaction mixture was filtered though a filter pad (Celite) to remove the catalyst and the filtrate was evaporated to dryness in vacuo. The solid residue was triturated with water, filtered and dried to yield 8 g (63% yield) of DL-1,2,3,4-tetrahydroisoquinolin-1-carboxylic acid. FD-Mass spectrum 178 (MH+); 1H NMR (DMSO-d6): δ 2.80-3.00 (m, 3H), 3.15 (m, 1H), 3.30-3.40 (m, 2H), 7.05-7.25 (m, 4H), 7.70 (m, 1H).

Workup

  1. filtrationThe reaction mixture was filtered though a filter pad (Celite)
  2. customto remove the catalyst
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe solid residue was triturated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-f358781de21a461aaa9d0d219a3aa6e9
Source dataset
uspto-grants-1993_10
Patent number
US05250660

Reaction notes

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