1,4-Naphthalenedione, 2-bromo- → HCID 10399257, compound

HRID 260762Notes

Reaction equation

HRID 260762 reaction equation
CN(C)[N:3]=[CH:4]/[CH:5]=[CH:6]/[CH2:7][CH3:8].Br[C:11]1[C:12](=[O:22])[C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.CC1C=CN=C2C(=O)C3C=CC=CC=3C(=O)C=12>C1(C)C(C)=CC=CC=1>[CH3:8][CH2:7][C:6]1[CH:5]=[CH:4][N:3]=[C:11]2[C:12]([C:13]3[C:18]([C:19](=[O:21])[C:20]=12)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:22]

Participants

5

Reactant 3

HCID 749441,4-Naphthalenedione, 2-bromo-HCID 4577324-Methylbenzo(g)quinoline-5,10-dioneHCID 86747024trans-2-Pentenal N,N-Dimethylhydrazone

Product 1

HCID 10399257HCID 10399257, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of trans-2-pentenal N,N-dimethylhydrazone (49.15 g, 0.39 mol) in xylene (100 mL) was quickly added to a xylene (600 mL) solution of 2-bromo-1,4-naphthoquinone (71.12 g, 0.30 mol) and the dark reaction heated at reflux for 6 h. Workup followed the procedure described above for cleistopholine. Chromatography provided pure homocleistopholine (13) (10.90 g, 14%). An analytical sample was obtained by crystallization from EtOAc: mp 157°-158° C.; IR (KBr) 1680, 1665, 1590, 1575, 1450, 1340, 1300, 1280, 1260, 1225, 1200, 1000, 955, 870, 850, 800, 790, 730 cm-1 ; 1H NMR (CDCl3) δ1.29 (t, 3 H, J=7.4 Hz), 3.28 (q, 2 H, J=7.4 Hz), 7.48 (d, 1 H, J=5.0 Hz), 7.71-7.78 (m, 2 H), 8.14-8.18 (m, 1 H), 8.25-8.28 (m, 1 H), 8.87 (d, 1 H, J=5.0 Hz); 13C NMR (CDCl3) 14.1 (3), 28.0 (2), 127.1 (1), 127.2 (1), 128.5 (0), 129.3 (1), 132.4 (0), 133.9 (0), 134.0 (1), 134.5 (1), 150.2 (0), 153.6 (1), 157.2 (0), 181.8 (0),

Workup

  1. customthe dark reaction
  2. temperatureheated
  3. temperatureat reflux for 6 h

Sources & evidence

ORD record
ord-43fae3c241974588915a6d2d3a0d1127
Source dataset
uspto-grants-1996_06
Patent number
US05530004

Reaction notes

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