Acetic Acid → HCID 18399687, compound

HRID 1018946Notes

Reaction equation

HRID 1018946 reaction equation
C(O[C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][C:22]([O:30][CH3:31])=[C:23]([O:28][CH3:29])[CH:24]=3)[C:19]=2[CH:32]=O)=[CH:11][CH:10]=1)C1C=CC=CC=1.[C:34]([OH:37])(=O)[CH3:35]>[Zn]>[CH3:29][O:28][C:23]1[C:22]([O:30][CH3:31])=[CH:21][C:20]2[C:19]3[CH:32]=[N:15][C:13]4[CH:14]=[CH:9][C:10]([O:37][CH2:34][C:35]5[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=5)=[CH:11][C:12]=4[C:18]=3[CH:27]=[CH:26][C:25]=2[CH:24]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 18399659HCID 18399659, compound

Product 1

HCID 18399687HCID 18399687, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

2-( 4-Benzyloxy-6-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde (100 mg, 0.23 mmol) was dissolved in glacial acetic acid (15 mL) and heated to reflux with zinc dust (163 mg, 2.5 mmol) for 3.5 h. Acetic acid was evaporated in vacuo and the residue was dissolved in chloroform. The solution was filtered through a celite bed and the filtrate was washed successively with saturated sodium bicarbonate solution and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed over 50 g of silica gel using 1:2 mixture respectively of hexanes and ethyl acetate to give the title compound as a white solid in 56% yield; 1H NMR(CDCl3) δ4.08(3H, s), 4.18(3H, s), 5.29(2H, s), 7.33(1H, s), 7.42(5H, m), 7.52(1H, d, J=8.9), 7.72(1H, d, J=2.6), 8.02(1H, d, J=8.9), 8.17(1H, s), 8.39(1H, d, J=8.9), 8.52(1H, d, J=8.9), 10.04(1H, s); 13C NMR(CDCl3) δ56.5, 56.6,70.8, 102.3, 108.6, 110.9, 112.8, 118.4, 119.6, 120.7, 124.2, 125.8, 127.7, 128.2, 128.6, 129.2, 131.4, 131.7, 137.1, 146.8, 148.6, 150.1, 151.2, 159.5; HRMS calcd for C26H24N3: 395.1521 , found: 395.1522.

Workup

  1. temperatureheated
  2. customAcetic acid was evaporated in vacuo
  3. dissolutionthe residue was dissolved in chloroform
  4. filtrationThe solution was filtered through a celite bed
  5. washthe filtrate was washed successively with saturated sodium bicarbonate solution and brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was chromatographed over 50 g of silica gel using 1:2 mixture respectively of hexanes and ethyl acetate

Sources & evidence

ORD record
ord-582a527de63449e4b0a658d3413fcad5
Source dataset
uspto-grants-2002_11
Patent number
US06486167B1

Reaction notes

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