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

HRID 1642113Notes

Reaction equation

HRID 1642113 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 acid

Procedure

3,4-Dihydroisoquinoline (20.0 g, 152 mmol) and malonic acid (15.9 g, 152 mmol) were mixed thoroughly at room temperature. The mixture was immersed in an oil bath preheated to 120° C., and was mixed further manually. After 30 min, no further evolution of gas was to be observed and the mixture was cooled to room temperature. The solid residue (29.0 g) was recrystallised directly from aqueous 2-propanol.

Workup

  1. customThe mixture was immersed in an oil bath
  2. custompreheated to 120° C.
  3. additionwas mixed further manually
  4. customThe solid residue (29.0 g) was recrystallised directly from aqueous 2-propanol

Sources & evidence

ORD record
ord-fa1552dcd86d4a00862c3424f1083fb2
Source dataset
uspto-grants-2012_02
Patent number
US08119633B2

Reaction notes

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