Acetyl chloride → Ethyl 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 1696548Notes

Reaction equation

HRID 1696548 reaction equation
[C:1](Cl)(=O)[CH3:2].[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][NH:11][CH:10]([C:16]([OH:18])=[O:17])[CH2:9]2>>[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[CH2:12][NH:11][CH:10]([C:16]([O:18][CH2:1][CH3:2])=[O:17])[CH2:9]2

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 27331741,2,3,4-Tetrahydro-6-hydroxy-3-isoquinolinecarboxylic acid

Product 1

HCID 14877974Ethyl 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylateYield 140.4%

Procedure

Acetyl chloride (30 mL, 33 g, 422 mmol) was added carefully to ice-cold anhydrous EtOH and the resulting solution was stirred at RT for 10 min. 6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (3.30 g, 14 mmol) was added and the mixture was stirred at 50° C. for 5 h. The solvent was evaporated and the residue was dried under vacuum to yield ethyl 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate (4.35 g, crude yield>100%) as a yellow solid. MS expected 222.1 found 222.0. 1H NMR (400 MHz, CD3OD): δ 7.06 (d, J=8.4 Hz, 1H), 6.74 (dd, J=8.0, and 2.4 Hz, 1H), 6.69 (d, J=2.4 Hz, 1H), 4.44-4.29 (m, 5H), 3.35 (dd, J=17.2, and 5.2 Hz, 1H), 3.15 (dd, J=17.2, and 11.6 Hz, 1H), 1.35 (t, J=7.2 Hz, 3H).

Workup

  1. stirringthe mixture was stirred at 50° C. for 5 h
  2. customThe solvent was evaporated
  3. customthe residue was dried under vacuum

Sources & evidence

ORD record
ord-47eb2166798645268b03371d0081ae11
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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