Acetic Acid → 1-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

HRID 1169365Notes

Reaction equation

HRID 1169365 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])=[CH:9][CH:8]=1.[C:22](O)(=O)C>>[Br:6][C:7]1[CH:8]=[C:9]2[C:10]([CH2:13][CH2:14][N:15]([C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[CH2:22]2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 1518036N-(4-Bromophenethyl)-2,2,2-trifluoroacetamide

Product 1

HCID 109688311-(7-Bromo-3,4-dihydroisoquinolin-2(1H)-yl)-2,2,2-trifluoroethanone

Procedure

Into acetic acid (42 ml) were added dropwise under ice cooling sulfuric acid (28 ml), subsequently N-(2-(4-bromophenyl)ethyl)trifluoroacetamide (7.8 g) and paraformamide (1.27 g) and the resulting mixture was stirred overnight under a nitrogen atmosphere. The reaction mixture was poured into ice water and was extracted with ethyl acetate. The organic layer was washed with an aqueous solution of sodium hydrogen carbonate, water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 7-bromo-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline (8.1 g) as a colorless oil.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous solution of sodium hydrogen carbonate, water
  3. dry with materialan aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate
  4. customThe resulting organic layer was evaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-4e4af0d4a3fe4a709ecb44076b75ba52
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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