Cyclohexene → 2-Cyano-4-methoxy-5-n-butoxy phenylamine

HRID 1801479Notes

Reaction equation

HRID 1801479 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:9]([O:17][CH3:18])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.C1CCCCC=1>C(O)C.[Pd]>[C:6]([C:5]1[CH:8]=[C:9]([O:17][CH3:18])[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:11][C:4]=1[NH2:1])#[N:7]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 583678172-Nitro-4-n-butoxy-5-methoxybenzonitrile

Product 1

HCID 583678162-Cyano-4-methoxy-5-n-butoxy phenylamineYield 71.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
40 °C

Procedure

2-nitro-4-butoxy-5-methoxybenzonitrile (0.563 g, 2.24 mmol), Pd/C (0.035 g) and anhydrous ethanol (25.0 mL) were added into a round bottom flask. The solution was stirred and heated under reflux. Cyclohexene (1.15 mL) was added and refluxed until the disappearance of the starting materials as monitored by TLC. After cooling, the resulting mixture was filtered and washed with ethanol. The filtrate was concentrated to yield a solid product. The crude product was suspended in anhydrous ethanol (4 ml), stirred and heated to 40° C. to react for 30 min, then cooled to room temperature, filtered and air-dried to yield 0.352 g of light yellow solid product with a recovery rate of 71%.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperaturerefluxed until the disappearance of the starting materials
  4. temperatureAfter cooling
  5. filtrationthe resulting mixture was filtered
  6. washwashed with ethanol
  7. concentrationThe filtrate was concentrated
  8. customto yield a solid product
  9. stirringstirred
  10. customto react for 30 min
  11. temperaturecooled to room temperature
  12. filtrationfiltered
  13. customair-dried

Sources & evidence

ORD record
ord-34679e767f1b449d86153eb8ddc75f2b
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

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