Formaldehyde → 1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

HRID 1534383Notes

Reaction equation

HRID 1534383 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.[CH2:13]=O>Cl>[CH2:13]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 2

HCID 712FormaldehydeHCID 6140L-Phenylalanine

Product 1

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

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of phenylalanine (40 g), formaldehyde (37% w/v in water, 91 ml) and concentrated hydrochloric acid (310 ml) was stirred and heated to reflux for 4 hours and then stored at ambient temperature for 16 hours. The precipitate was filtered off, washed with cold water and with acetone to give 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (11 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed with cold water and with acetone

Sources & evidence

ORD record
ord-c65a156d200d43efb57e3a9b8d905616
Source dataset
uspto-grants-1992_02
Patent number
US05089495

Reaction notes

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