Cyclohexene → 2-Amino-4-(3-chloropropoxy)-5-methoxybenzonitrile

HRID 1801487Notes

Reaction equation

HRID 1801487 reaction equation
[N+:1]([C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[C:9]([O:17][CH3:18])=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.C1CCCCC=1>C(O)C.[Pd]>[NH2:1][C:4]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][Cl:16])[C:9]([O:17][CH3:18])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 534163664-(3-Chloropropoxy)-5-methoxy-2-nitrobenzonitrile

Product 1

HCID 534010272-Amino-4-(3-chloropropoxy)-5-methoxybenzonitrileYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A mixture of 2-nitro-4-chloropropoxy-5-methoxy-benzonitrile (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 at 40° C. to react for 30 min, then cooled to room temperature, filtered and air-dried to yield light yellow solid product (0.352 g) with a recovery rate of 71%.

Workup

  1. additionwere added into a round bottom flask
  2. temperatureheated
  3. temperatureunder reflux
  4. temperaturerefluxed until the disappearance of the starting materials
  5. temperatureAfter cooling
  6. filtrationthe resulting mixture was filtered
  7. washwashed with ethanol
  8. concentrationThe filtrate was concentrated
  9. customto yield a solid product
  10. stirringstirred at 40° C.
  11. customto react for 30 min
  12. filtrationfiltered
  13. customair-dried

Sources & evidence

ORD record
ord-ed492ef8174f4dbfa80f68fb1ee53b2d
Source dataset
uspto-grants-2013_01
Patent number
US08349835B2

Reaction notes

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