1,4-Naphthoquinone → HCID 66647049, compound

HRID 1914796Notes

Reaction equation

HRID 1914796 reaction equation
CN([CH:4]=[CH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7])C.[CH:18]1[CH:29]=[C:28]2[C:21]([C:22]([CH:24]=[CH:25][C:26]2=[O:27])=[O:23])=[CH:20][CH:19]=1>C(O)(=O)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([C:6]([C:5]2[C:24]3[CH:25]=[C:26]([OH:27])[C:28]4[C:21](=[CH:20][CH:19]=[CH:18][CH:29]=4)[C:22]=3[O:23][CH:4]=2)=[O:7])[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 85301,4-NaphthoquinoneHCID 1481361(E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

Product 1

HCID 66647049HCID 66647049, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of enaminone 12 (2.0 g, 8.43 mmol) and NQ-1 (1.33 g, 8.43 mmol) in acetic acid (20 ml) was stirred at room temperature for 5 h under an atmosphere of N2. The resulting precipitate was filtered, washed with water, and dried under high vacuum to afford compound 24 (1.5 g, 50%) as an off-white solid. TLC Rf=0.5 (petroleum ether-EtOAc, 5:5); 1H NMR (DMSO-d6) δ 8.72 (s, 1H), 8.28 (d, J=8.3 Hz, 1H), 8.22 (d, J=8.3 Hz, 1H), 7.70 (app t, 1H), 7.60-7.50 (band, 4H), 7.15 (d, J=8.3 Hz, 1H), 3.89 (s, 3H), 3.87 (s, 3H); MS (ES) m/z 349 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-7db4c4ca4ad64e2593a4f4d9002dcb55
Source dataset
uspto-grants-2013_12
Patent number
US08614237B2

Reaction notes

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