HCID 18399677, compound → HCID 9819012, compound

HRID 1018952Notes

Reaction equation

HRID 1018952 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[C:6]([N+:10]([O-])=O)[C:5]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:25][CH3:26])=[C:18]([O:23][CH3:24])[CH:19]=4)[C:14]=3[CH:27]=O)=[CH:4][C:3]=2[O:2]1>C(O)(=O)C.[Zn]>[CH3:24][O:23][C:18]1[C:17]([O:25][CH3:26])=[CH:16][C:15]2[C:14]3[CH:27]=[N:10][C:6]4[CH:7]=[C:8]5[O:9][CH2:1][O:2][C:3]5=[CH:4][C:5]=4[C:13]=3[CH:22]=[CH:21][C:20]=2[CH:19]=1

Participants

4

Reactant 1

HCID 18399677HCID 18399677, compound

Product 1

HCID 9819012HCID 9819012, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(3,4-methylenedioxy-6-nitrophenyl)-6,7-dimethoxy-1-naphthaldehyde (46 mg, 0.12 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 (32 mg, 80%); mp 171-171° C. IR (KBr) 1610, 1461, 1277; 1H NMR (CDCl3), δ4.06 (3H, s), 4.15 (3H, s), 6.15 (2H, s) 7.27 (11, s). 7.54 (1H, s), 7.85(11H, s), 7.94 (1H, d, J=8.7), 8.09(1H, s), 8.15 (1H, d, J=8.7), 9.88 (1H, s); 13C NMR (CDCl3) δ56.4, 56.6, 99.7, 102.3, 102.4, 107.7, 108.5, 118.5, 21.0, 121.2, 125.6, 127.7, 130.8, 131.2, 142.8, 145.9, 148.8, 149.7, 150.1; HRMS calcd for C20H15NO4+H; 334,.1079.

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-73e9956bdc274357a3f864018aca6237
Source dataset
uspto-grants-2002_11
Patent number
US06486167B1

Reaction notes

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