7-Methoxy-3,4-dihydronaphthalene-1-carbonitrile → 7-Methoxynaphthalene-1-carbonitrile

HRID 1830669Notes

Reaction equation

HRID 1830669 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1>CC1C=CC(C(C)C)=CC=1.CCCCCC.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[C:13]#[N:14])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 115212017-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

Product 1

HCID 113443927-Methoxynaphthalene-1-carbonitrileYield 44.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolventHCID 8058HexaneSolvent

Conditions

Temperature
150 °C

Procedure

To a mixture of 7-methoxy-3, 4-dihydronaphthalene-1-carbonitrile (9.95 g, 53.1 mmol) in p-cymene (1600 mLs) was added 10% Pd/C (5 g), the reaction mixture was stirred and heated to 150° C. overnight. The mixture was cooled and the catalyst removed by filtering through filter aid. The p-cymene was removed on the rotovap with the vacuum pump, giving a liquid which solidified on standing. The solid was slurried in hexane, filtered and dried to afford a-white solid (4.3 g, 44%). A portion was purified further by silica gel (10% ethyl acetate-hexanes) to produce a white solid: mp 77–78° C.; 1H NMR (DMSO-d6): δ 3.97 (3H, s), 7.36 (1H, s), 7.39 (1H, d, J=2.5 Hz), 7.52 (1H, t, J=7.4 Hz), 8.04–8.13 (2H, m), 8.24 (1H, d, J=8.2 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. customthe catalyst removed
  3. filtrationby filtering
  4. filtrationthrough filter aid
  5. customThe p-cymene was removed on the rotovap with the vacuum pump
  6. customgiving a liquid which
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-aad5b78c7ee24cfc875046f3cdcc11ef
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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