Dimethylformamide → 1,2,3,4-tetrahydro-2-[2-nitro-4-(trifluoromethyl)phenyl]isoquinoline

HRID 2099112Notes

Reaction equation

HRID 2099112 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1.CN(C)C=O.F[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>O>[N+:27]([C:18]1[CH:19]=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70461,2,3,4-TetrahydroisoquinolineHCID 677784-Fluoro-3-nitrobenzotrifluoride

Product 1

HCID 27970331,2,3,4-tetrahydro-2-[2-nitro-4-(trifluoromethyl)phenyl]isoquinolineYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,2,3,4-tetrahydroisoquinoline (909 μl, 7.26 mmol, commercially available product) was added at 0° C. to an N,N-dimethylformamide (DMF; 4 ml) solution of 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (506 g, 2.42 mmol, commercially available product). The resulting mixture was warmed to room temperature and stirred for 3.5 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=10/1). Thus, 1,2,3,4-tetrahydro-2-[2-nitro-4-(trifluoromethyl)phenyl]isoquinoline (779 mg, 99.9%) was yielded as an orange-colored solid.

Workup

  1. extractionthe resulting mixture was extracted three times with ethyl acetate
  2. washThe obtained organic layer was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-dac6d2d29af44b7e8f13dcc13c509214
Source dataset
uspto-grants-2009_08
Patent number
US07569536B2

Reaction notes

Loading…