Formaldehyde → (2-Methyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol

HRID 2081497Notes

Reaction equation

HRID 2081497 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]([CH2:11][OH:12])[NH:2]1.C=O.[Na].[C:16](=O)([O-])[O-].[K+].[K+]>C(O)=O>[CH3:16][N:2]1[CH:3]([CH2:11][OH:12])[CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 3752277(1,2,3,4-Tetrahydro-isoquinolin-3-yl)-methanolHCID 5360545Sodium

Product 1

HCID 589740(2-Methyl-1,2,3,4-tetrahydroisoquinolin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
140 °C

Procedure

In a sealed tube, a mixture of 1.80 g of 1,2,3,4-tetrahydro-3-isoquinolinemethanol, 1.69 g of 90% formic acid and 1.04 g of 35% formalin was heated at 140° C. for 16 hours. The reaction solution was cooled and then made alkaline by addition of 10% aqueous sodium solution. Subsequently, potassium carbonate was added to the solution and a precipitated oil was extracted with chloroform. The extract was dried over anhydrous sodium sulfate and placed under reduced pressure to remove the solvent. There was obtained 1.95 g of 2-methyl-1,2,3,4-tetrahydro-3-isoquinolinemethanol.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractiona precipitated oil was extracted with chloroform
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customto remove the solvent

Sources & evidence

ORD record
ord-5a05dda084ce464681427f416f392cdf
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

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