3-(2-Aminoethyl)phenol hydrochloride → Ethyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate hydrochloride

HRID 2202209Notes

Reaction equation

HRID 2202209 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=O.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1.CCO>[ClH:1].[OH:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH:13]([C:12]([O:16][CH2:17][CH3:18])=[O:15])[NH:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 770013-(2-Aminoethyl)phenol hydrochlorideHCID 86599969Ethyl glyoxylate toluene

Product 1

HCID 19865448Ethyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate hydrochlorideYield 90.1%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A solution of 3-(2-aminoethyl)phenol hydrochloride (4.60 g, 26.49 mmol) and 47% ethyl glyoxylate/toluene solution (polymer form) (6.15 mL, 29.14 mmol) in a mixed solvent of toluene/EtOH (50 mL) was heated under reflux for 18 hr. The reaction mixture was concentrated under reduced pressure. The precipitate was collected by filtration, and washed with ethyl acetate/diethyl ether to give ethyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylate hydrochloride (6.15 g, 23.86 mmol, 90%) as a white powder.

Workup

  1. temperatureunder reflux for 18 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ethyl acetate/diethyl ether

Sources & evidence

ORD record
ord-53a8838a2c164503a4106c4f49a4b39a
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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