1,4-Naphthalenedione, 2-bromo- (9CI) → HCID 10399257, compound

HRID 483835Notes

Reaction equation

HRID 483835 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- (9CI)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) δ 1.29 (t, 3H, J=7.4 Hz), 3.28 (q, 2H, J=7.4 Hz), 7.48 (d, 1H, J=5.0 Hz), 7.71-7.78 (m, 2H), 8.14-8.18 (m, 1H), 8.25-8.28 (m, 1H), 8.87 (d, 1H, 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), 184.5 (0) ppm; Anal. calcd for C15H11NO2 : C 75.94, H 4.67, N 5.90; found C 75.85, H, 4.68, N 5.91.

Workup

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

Sources & evidence

ORD record
ord-9dabb66510dc432abfa5f4f949acb1c5
Source dataset
uspto-grants-1993_07
Patent number
US05227383

Reaction notes

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