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

HRID 2304006Notes

Reaction equation

HRID 2304006 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

Conditions

Temperature
60 °C

Procedure

A mixture containing 6.62 g of 3,4-dihydroisoquinoline and 5.13 of malonic acid is triturated in an oil bath at 120° C. The mixture thickens and becomes entirely solid; it is worked into a powder with a spatula. The total duration of heating is about 40 minutes. The mixture is cooled to about 60° C. and treated with 120 ml of MeOH and 20 ml of water, which dissolves the medium. A first crop is obtained under cold conditions and a second crop is then obtained by evaporating the filtrate and crystallizing the residue from acetone.

Workup

  1. customis triturated in an oil bath at 120° C
  2. temperatureThe total duration of heating
  3. additiontreated with 120 ml of MeOH and 20 ml of water, which
  4. dissolutiondissolves the medium
  5. customA first crop is obtained under cold conditions
  6. customa second crop is then obtained
  7. customby evaporating the filtrate
  8. customcrystallizing the residue from acetone

Sources & evidence

ORD record
ord-b14e6390db3a40058fd2d72bdf2dbe6a
Source dataset
uspto-grants-2002_08
Patent number
US06433185B1

Reaction notes

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