Nitric Acid → HCID 15066355, compound

HRID 1165811Notes

Reaction equation

HRID 1165811 reaction equation
C([N:8]([C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:20])[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)(C(OCC)=O)=O.[N+:26]([O-:29])(O)=[O:27]>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:19]([NH:8][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][C:12]=2[N+:26]([O-:29])=[O:27])[CH:17]=[CH:18][C:9]=1[NH:8][C:19]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:20])([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:20]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 19861005HCID 19861005, compound

Product 1

HCID 15066355HCID 15066355, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

A partial suspension of 1 2-diethoxalylaminonaphthalene (1,79 g, 5 mmol) in 7 ml of acetic acid and 7 ml of acetic anhydride was treated dropwise with a solution of nitric acid (1.8 ml, 43 mmol, d 1.52) in 7 ml of acetic acid, with stirring at 0° C. The resulting solution was stirred at 0° C. for 11/2 h and then poured on 150 ml of ice/water. The yellow precipitate was isolated, dried and recrystallized from ethanol with decolourising carbon giving 0.67 g (33%) of the required compound, m.p. 173-175° C.,1H-NMR (CDCl3 +DMSO-d6), 1,43 (t,J=7 Hz, 6H,2 CH3), 4.40 (q,J=7Hz, 2H, CH2), 4.42 (q,J=7Hz, 2H, CH2), 7.3-8.4 (m, 5H, ArH).

Workup

  1. stirringThe resulting solution was stirred at 0° C. for 11/2 h
  2. customThe yellow precipitate was isolated
  3. customdried
  4. customrecrystallized from ethanol with decolourising carbon giving 0.67 g (33%) of the required compound, m.p. 173-175° C.,1H-NMR (CDCl3 +DMSO-d6), 1,43 (t,J=7 Hz, 6H,2 CH3), 4.40 (q,J=7Hz, 2H, CH2), 4.42 (q,J=7Hz, 2H, CH2), 7.3-8.4 (m, 5H, ArH)

Sources & evidence

ORD record
ord-5d0e9287015d4035a33f6c604eed7d56
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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