Malonic Acid → (1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acid

HRID 1828772Notes

Reaction equation

HRID 1828772 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][N:2]=1.C(O)(=O)[CH2:12][C:13]([OH:15])=[O:14]>>[CH:1]1([CH2:12][C:13]([OH:15])=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1

Participants

3

Reactant 2

HCID 867Malonic AcidHCID 767053,4-Dihydroisoquinoline

Product 1

HCID 2733683(1,2,3,4-Tetrahydroisoquinolin-1-yl)acetic acidYield 48%

Conditions

Temperature
120 °C

Procedure

3,4-Dihydroisoquinoline (147) (2.2 g, 16.77 mmol) and malonic acid (1.94 g, 16.77 mmol) were mixed at room temperature and heated at 120° C. for 1 hour in an oil bath. The mixture was then allowed to cool to room temperature, and the product was recrystallised from methanol (150 ml). Drying gave a colourless solid (1.52 g, 7.99 mmol, 48%).

Workup

  1. temperatureto cool to room temperature
  2. customthe product was recrystallised from methanol (150 ml)
  3. customDrying

Sources & evidence

ORD record
ord-f413eac8cd34435eb595b3471f0f6361
Source dataset
uspto-grants-2006_06
Patent number
US07060707B2

Reaction notes

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