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

HRID 1418730Notes

Reaction equation

HRID 1418730 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-a939a188a4e9477593b582b308d71426
Source dataset
uspto-grants-1999_03
Patent number
US05883270

Reaction notes

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