Hydrochloric Acid → 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

HRID 615694Notes

Reaction equation

HRID 615694 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[CH2:14]=O>>[CH2:14]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]([C:10]([OH:12])=[O:11])[NH:1]1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712Formaldehyde2×HCID 6140L-Phenylalanine

Product 1

HCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Procedure

Phenylalanine (75 g) was refluxed with 488 ml of concentrated HCl and 165 ml of formalin for 30 minutes. Then a further 165 ml of HCl and 75 ml of formalin were added and the mixture refluxed for six more hours. After cooling, it was filtered, washed with a small amount of methanol, and dried overnight in a vacuum oven. This material was then treated for an hour with refluxing isopropanol and filtered after cooling to give 28 gms.

Workup

  1. temperaturethe mixture refluxed for six more hours
  2. temperatureAfter cooling
  3. filtrationit was filtered
  4. washwashed with a small amount of methanol
  5. customdried overnight in a vacuum oven
  6. additionThis material was then treated for an hour with refluxing isopropanol
  7. filtrationfiltered
  8. temperatureafter cooling
  9. customto give 28 gms

Sources & evidence

ORD record
ord-e96d8db868e642da82dea8f17c255655
Source dataset
uspto-grants-1985_02
Patent number
US04500713

Reaction notes

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