HCID 18399655, compound → HCID 18399694, compound

HRID 1018951Notes

Reaction equation

HRID 1018951 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([O:24][CH3:25])=[C:17]([O:22][CH3:23])[CH:18]=3)[C:13]=2[CH:26]=O)=[CH:5][CH:4]=1>C(O)(=O)C.[Zn]>[CH3:23][O:22][C:17]1[C:16]([O:24][CH3:25])=[CH:15][C:14]2[C:13]3[CH:26]=[N:9][C:7]4[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=4[C:12]=3[CH:21]=[CH:20][C:19]=2[CH:18]=1

Participants

4

Reactant 1

HCID 18399655HCID 18399655, compound

Product 1

HCID 18399694HCID 18399694, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(4-methoxy-6-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde (30 mg, 0.81 mmol) in acetic acid (3 ml) and zinc dust (100 mg, 1.5 mmol) was heated to reflux for 3 hours. Acetic acid was evaporated in vacuo and the residue extacted with chloroform. The chloroform solution was filtered through a celite bed. The filtrate was washed successively with saturated sodium bicarbonate solution and brine and evaporated to dryness. The residue obtained was chromatographed on 75 g silica using a 1:1 mixture of hexanes:ethyl acetate as eluent to give the title compound (20 mg, 77%); IR (KBr) 1615, 1518, 1272; 1H NMR (CDCl3) δ4.02 (3H, s), 4.08 (3H, s), 4.18 (3H, s), 7.33 (1H, s), 7.37 (1H, dd, J=9.1, 2.6 Hz), 7.54 (1H, d, J=2.6), 8.05 (1H, d, J=8.7), 8.42 (1H, d, J=8.7), 8.56 (1H, d, J=9.1), 10.05 (1H, s); 13C NMR δ56.1, 56.5, 56.6, 102.2, 108.6, 109.5, 119.0, 119.2, 119.3, 120.6, 124.1, 125.8, 127.6, 131.4, 131.7, 146.7, 148.4, 150.1, 151.1, 160.3; HRMS calcd for C24H12NO3; 319.1208; found 319.1209.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. customAcetic acid was evaporated in vacuo
  4. filtrationThe chloroform solution was filtered through a celite bed
  5. washThe filtrate was washed successively with saturated sodium bicarbonate solution and brine
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customwas chromatographed on 75 g silica using
  9. additiona 1:1 mixture of hexanes

Sources & evidence

ORD record
ord-2314f3e3b6894bc5bc97201aba93955a
Source dataset
uspto-grants-2002_11
Patent number
US06486167B1

Reaction notes

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