5-Iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline → 5-Chloro-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494198Notes

Reaction equation

HRID 494198 reaction equation
IC1C=C([N+]([O-])=O)C=C2C=1CCCN2C(=O)C(F)(F)F.[Cl:21][C:22]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[C:28]2[C:23]=1[CH2:24][CH2:25][CH2:26][N:27]2C(=O)C(F)(F)F>CN(C=O)C.[Cu]Cl>[Cl:21][C:22]1[CH:31]=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[C:28]2[C:23]=1[CH2:24][CH2:25][CH2:26][NH:27]2

Participants

5

Reactant 2

HCID 858563405-Iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinolineHCID 858563425-Chloro-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline

Product 1

HCID 690396025-Chloro-7-nitro-1,2,3,4-tetrahydroquinoline

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-iodo-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D53P) (1.69 g, 6.73 mmol) in DMF (25 ml) was treated with copper (I) chloride (1.66 g, 16.8 mmol) at 130C. for 7 h. On cooling the solution was filtered and the filtrate concentrated in vacuo. The residue was dissolved in EtOAc and washed with 5M HCl, then dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography to give a (1:1) mixture of the title compound and 5-chloro-7-nitro-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (591 mg). This mixture was treated with potassium carbonate in methanol to yield the title compound (450 mg) as a brown solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.49 (d, 1H), 7.19 (d, 1H), 4.31 (br.s, 1H), 3.33 (m, 2H), 2.82 (t, 2H), 1.98 (m, 2H).

Workup

  1. temperatureOn cooling the solution
  2. filtrationwas filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with 5M HCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography
  9. customto give

Sources & evidence

ORD record
ord-dd0093a942d9478b9d72586998388ae0
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Reaction notes

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