Sodium Acetate → 8-Methoxy-1,2,3,4-tetrahydronaphthalene-1,2-dinitrile

HRID 5352Notes

Reaction equation

HRID 5352 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([C:16]#[N:17])[CH:7]2[C:14]#[N:15].CC([O-])=O.[Na+]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][CH:2]=[C:3]2[C:8]=1[CH:7]([C:14]#[N:15])[CH:6]([C:16]#[N:17])[CH2:5][CH2:4]2

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 156623805-Bromo-8-methoxy-1,2,3,4-tetrahydronaphthalene-1,2-dinitrile

Product 1

HCID 156623818-Methoxy-1,2,3,4-tetrahydronaphthalene-1,2-dinitrileYield 85.1%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

The product from Example 53 (2.90 g) was treated with 3.0 g 10% Pd/BaSO4 and 1.36 g NaOAc in 250 ml methanol and hydrogenated at 4 atm for 4 h. The reaction was filtered and evaporated; and the product was dissolved in ethyl acetate, washed with 5% NaHCO3, dried (MgSO4), and evaporated to yield 1.80 g of the desired product as a colorless oil. NMR (CDCl3) δ 2.30 (m, 2H), 2.80-3.20 (m, 3H), 3.91 (s, 3H), 4.39 (d, 1/3H), 4.46 (d, 2/3H), 6.87 (m, 2H), 7.27 (m, 1H).

Workup

  1. filtrationThe reaction was filtered
  2. customevaporated
  3. dissolutionand the product was dissolved in ethyl acetate
  4. washwashed with 5% NaHCO3
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-cc146a0b13854115a3294a70fa64f354
Source dataset
uspto-grants-1993_09
Patent number
US05244888

Reaction notes

Loading…