Hydrochloric Acid → 2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

HRID 2396091Notes

Reaction equation

HRID 2396091 reaction equation
[C:1]([CH:4]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][NH:5]1)([OH:3])=[O:2].[CH2:14]=O.Cl>C(O)=O.O>[CH3:14][N:5]1[CH:4]([C:1]([OH:3])=[O:2])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 954891,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 31574912-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidYield 53%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 0.364 g (2.07 mmol) of 3-carboxy-1,2,3,4-tetrahydroisoquinoline in 25 mL of formic acid was combined with 2.5 mL of 37% formaldehyde. The resulting mixture was allowed to reflux for approximately 17 hours. After cooling, the mixture was contentrated under reduced pressure to provide a gum. This gum was dissolved in 3.0 mL of water, adjusted to a pH 2 using hydrochloric acid and then purified using ion-exchange chromatography (Dowex 50x-8, 100 meshcation) to provide 0.21 g of a yellow powder.

Workup

  1. temperatureto reflux for approximately 17 hours
  2. temperatureAfter cooling
  3. customto provide a gum
  4. custompurified

Sources & evidence

ORD record
ord-48c5d17730484c9a9ff0a3b1be191a71
Source dataset
uspto-grants-1996_02
Patent number
US05491166

Reaction notes

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