o-Iodonitrobenzene → 6-(2-Nitrophenyl)-2,3-dimethoxy-7,8-dihydronaphthalene

HRID 1582869Notes

Reaction equation

HRID 1582869 reaction equation
C([O-])(=O)C.[Na+].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[CH:14]=[CH:13][CH2:12][CH2:11]2.I[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>CC(N(C)C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N+:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:12]1[CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([O:18][CH3:19])[C:8]([O:7][CH3:6])=[CH:9][C:10]=2[CH:11]=1)([O-:29])=[O:28]

Participants

6

Reactant 3

HCID 69115o-IodonitrobenzeneHCID 517045Sodium AcetateHCID 127653926,7-Dimethoxy-3,4-dihydronaphthalene

Product 1

HCID 227164386-(2-Nitrophenyl)-2,3-dimethoxy-7,8-dihydronaphthaleneYield 29%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
140 °C

Procedure

Pd(PPh3)2Cl2 (840 mg, 1.2 mmol) and sodium acetate (200 mg, 2.4 mmol) were added to a solution of 6,7-dimethoxy-3,4-dihydronaphthalene (2, 700 mg, 3.7 mmol) and 1-iodo-2-nitrobenzene (925 mg, 3.7 mmol) in dimethylacetamide (50 mL). The mixture was stirred under nitrogen at 140° C. overnight, and then concentrated in vacuo. Ethyl acetate (60 mL) was added to the residue and washed with distilled water (50 mL). The organic layer was separated and passed through a celite bed. The organic layer was then washed with brine, dried (anhydrous Na2SO4) and concentrated in vacuo. The residue was chromatographed to give compound 3 (330 mg) in 29% yield; 1H NMR (CDCl3) d 2.51(2H, t, J=8.1), 2.92(2H, t, J=8.1), 3.87(3H, s), 3.90(3H, s), 6.45(1H, s), 6.67(1H, s), 6.73(1H, s), 7.38˜7.45 (2H, m), 7.54˜7.62(1H, m), 7.88˜7.93(1H, m); 13C NMR d 28.5, 28.5, 56.6, 111.0, 111.7, 124.9, 127.0, 127.1, 128.1, 128:3, 131.3, 133.3, 135.7, 138.7, 147.9, 148.9.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEthyl acetate (60 mL) was added to the residue
  3. washwashed with distilled water (50 mL)
  4. customThe organic layer was separated
  5. washThe organic layer was then washed with brine
  6. dry with materialdried (anhydrous Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed

Sources & evidence

ORD record
ord-360bed0cdf194b48b7a07eaaa8279644
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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