Pentylamine → 4-(Pentylamino)naphthalene-1,2-dione

HRID 1601420Notes

Reaction equation

HRID 1601420 reaction equation
CO[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[C:5](=[O:14])[CH:4]=1.[CH2:15]([NH2:20])[CH2:16][CH2:17][CH2:18][CH3:19]>C(O)C>[CH2:15]([NH:20][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[C:5](=[O:14])[CH:4]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 8060PentylamineHCID 594762HCID 594762, compound

Product 1

HCID 218316514-(Pentylamino)naphthalene-1,2-dioneYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 650 mg (3.45 mmol) of 4-methoxy-1,2-naphthoquinone in 20 mL of ethanol was added 0.80 mL (6.90 mmol) of pentylamine. The reaction mixture was stirred at room temperature for 60 min. The resulting red precipitate was collected by filtration and then triturated with 20 mL of ethyl acetate to afford 411.7 mg (49%) of 4-pentylamino-1,2-naphthoquinone, which was recrystallized from ethyl acetate: mp>215° C.; 1H NMR (300 MHz, CDCl3, TMS) δ 8.21 (dd, J=7.5, 1.6 Hz, 1H), 7.69 (td, J=7.7, 1.6 Hz, 1H), 7.61 (t, J=7.5 Hz, 1H), 7.49 (d, J=7.9 Hz, 1H), 5.86 (s, 1H), 5.76 (br s, 1H), 3.4-3.3 (m, 2H), 1.8-1.7 (m, 4H), 1.5-1.4 (m, 4H), 0,95 (t, J=7 Hz, 3H); 13C NMR (75.5 MHz, d6 -DMSO, TMS) δ 182.0, 174.7, 154.8, 134.1, 131.2, 130.8, 127.8, 123.3, 98.0, 43.1, 28.7, 27.4, 21.8, 13.9. Analysis calculated for C15H17NO2 : C=74.04, H=7.06, N=5.7; Found: C=73.88, H=7.01, N=5.73.

Workup

  1. filtrationThe resulting red precipitate was collected by filtration
  2. customtriturated with 20 mL of ethyl acetate

Sources & evidence

ORD record
ord-4832db768cdb4edc90714403d199d499
Source dataset
uspto-grants-1999_11
Patent number
US05977187

Reaction notes

Loading…