HCID 178418361, compound → 5-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 1645896Notes

Reaction equation

HRID 1645896 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[H][H]>CC(O)=O.[Pd]>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH2:5][CH2:4][NH:3][C:2]2=[O:1]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178515888HCID 178515888, compound

Product 1

HCID 132366635-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-oneYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 10.0 g (62.0 mmol) of 1,5-dihydroxyisoquinoline in 500 ml of HOAc and 2 g of 20% Pd-C was hydrogenated at room temperature until the required amount of hydrogen was absorbed. The solution was filtered and concentrated. The resulting solid was recrystallized from water (200 ml) to give 8.74 g (86%) of product; mp 195°-198°.

Workup

  1. customwas hydrogenated at room temperature
  2. customwas absorbed
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. customThe resulting solid was recrystallized from water (200 ml)

Sources & evidence

ORD record
ord-accc70bf28c4442f80c41e623ae64975
Source dataset
uspto-grants-1993_01
Patent number
US05177075

Reaction notes

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