1-Iodo-4-nitrobenzene → HCID 22181611, compound

HRID 2217596Notes

Reaction equation

HRID 2217596 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[C:13](=[O:18])[NH:14][CH:15]=[CH:16][CH:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N>CCOC(C)=O.[Cu]I.O1CCOCC1>[CH3:11][C:12]1[C:13](=[O:18])[N:14]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:15]=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 124951-Iodo-4-nitrobenzeneHCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 704812-Hydroxy-3-methylpyridine

Product 1

HCID 22181611HCID 22181611, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

1-Iodo-4-nitrobenzene (1.61 g, 6.45 mmol) was combined with 3-methyl-2-pyridone (0.845 g, 7.74 mmol), CuI (0.246 g, 1.29 mmol), and K3PO4 (2.74 g, 12.9 mmol). 1,4-Dioxane (6 mL) was added followed by trans-1,2-diaminocyclohexane (0.194 mL, 1.61 mmol). The mixture was heated to reflux for 19 h before cooling and diluting with EtOAc. The mixture was filtered through a plug of silica, eluting with EtOAc, and the filtrate concentrated under reduced pressure. Purification of the crude product by flash chromatography provided 159-a (0.528 g, 36%) as a brown solid. MS: APCI (AP+): 231.1 (M)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 19 h
  3. temperaturebefore cooling
  4. filtrationThe mixture was filtered through a plug of silica
  5. washeluting with EtOAc
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customPurification of the crude product by flash chromatography

Sources & evidence

ORD record
ord-6392b6cba8d54e6d877be258a718e356
Source dataset
uspto-grants-2008_08
Patent number
US07407974B2

Reaction notes

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