Cyclohexene → HCID 67399433, compound

HRID 711893Notes

Reaction equation

HRID 711893 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:8]=1[C:9]#[N:10].C1CCCCC=1>CCO.[Pd]>[NH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:8]=1[C:9]#[N:10]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 67400515HCID 67400515, compound

Product 1

HCID 67399433HCID 67399433, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(3-methoxypropylamino)-6-nitrobenzonitrile (Example 258c) (0.58 g, 2.48 mmol) in EtOH (20 mL) was added cyclohexene (1.26 mL, 12.4 mmol). Then 10% Pd/C (1.32 g) was added, and the reaction mixture was refluxed at 100° C. for 20 minutes, cooled to room temperature, filtered trough Celite which was washed with EtOH (3×20 mL), and evaporated to give 2-amino-6-(3-methoxypropylamino)benzonitrile (0.43 g, 84%) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ 1.71-1.77 (m, 2H), 3.10 (q, J=6.8 Hz, J=6.8 Hz, 2H), 3.22 (s, 3H), 3.37 (t, J=3.2 Hz, 2H), 5.55 (t, J=5.2 Hz, NH), 5.63 (s, NH2), 5.79 (d, J=7.6 Hz, 1H), 5.93 (d, J=8.0 Hz, 1H), 6.98 (t, J=8.0 Hz, 1H). MS 206 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered trough Celite which
  3. washwas washed with EtOH (3×20 mL)
  4. customevaporated

Sources & evidence

ORD record
ord-d8a23ae841e244f383e985b1b55524c5
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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