Dimethylformamide → 2-Trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol

HRID 1416355Notes

Reaction equation

HRID 1416355 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2.C[O:13][C:14](=O)[C:15]([F:18])([F:17])[F:16].CN(C=O)C>ClCCl>[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:14](=[O:13])[C:15]([F:18])([F:17])[F:16])[CH2:7]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 9893Methyl trifluoroacetateHCID 139482511,2,3,4-Tetrahydroisoquinolin-5-ol

Product 1

HCID 154910662-Trifluoroacetyl-1,2,3,4-tetrahydro-5-isoquinolinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.35 g (15.9 mmol) 5-hydroxy-1,2,3,4-tetrahydroisoquinoline, 1.92 mL (19.0 mmol) methyltrifluoroacetate and 15 mL DMF were mixed and stirred for over night at room temperature. The reaction mixture was diluted with dichloromethane, washed with water containing one drop of dil. hydrochloric acid and with aqueous sodium chloride. After drying over Na2SO4 and evaporation to dryness, the product was purified by silicagel chromatography (system C). Yield quantitative. 1H NMR (CDCl3, 400 MHz): 8.15 (1H, bd), 7.06 (1H, t, 8.1 Hz), 6.6-6.9 (2H, m), 4.75 (2H, ss), 3.86 (2H, m), 2.90 (2H, m).

Workup

  1. washwashed with water containing one drop of dil. hydrochloric acid and with aqueous sodium chloride
  2. dry with materialAfter drying over Na2SO4 and evaporation to dryness
  3. customthe product was purified by silicagel chromatography (system C)
  4. customYield quantitative

Sources & evidence

ORD record
ord-fc8fe3c63c9d4d1b96b9ab8f07f52480
Source dataset
uspto-grants-1999_06
Patent number
US05912342

Reaction notes

Loading…