Nitric Acid → HCID 15066357, compound

HRID 1165814Notes

Reaction equation

HRID 1165814 reaction equation
[C:1]([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]=1[N+:19]([O-:21])=[O:20])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[N+:22]([O-])([OH:24])=[O:23]>S(=O)(=O)(O)O>[C:1]([NH:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[C:12]([N+:22]([O-:24])=[O:23])[CH:13]=[CH:14][CH:15]=2)[C:10]=1[N+:19]([O-:21])=[O:20])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 15066356HCID 15066356, compound

Product 1

HCID 15066357HCID 15066357, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

2-Ethoxalylamino-1-nitronaphthalene (11.5 g, 0.04 mol) was dissolved in 80 ml of sulfuric acid (d 1.84)by portionwise addition, with vigorous stirring on an ice-bath. Nitric acid (1.66 ml, 0.04 mol, d 1.52) in 20 ml of sulfuric acid (d 1.84) was added dropwise during 1 h at 0° C., and the mixture was stirred at this temperature for a further hour. The mixture was cautiously poured into 600 ml of ice/water with vigorous stirring. The yellow solid was collected, washed with water, and boiled with 300 ml of ethanol. The hot suspension was filtered and the undissolved residue was washed with 200 ml of ether to yield 7.35 g (55%) of the title compound, m.p. 232.7-233.4° C. (acetic acid),1H-NMR (DMSO-d6) 1.33 (t,J=7Hz,3H,CH3), 4.34 (q,J=7Hz,2H,CH2), 7.7-8.6 (m,5H,ArH), 11.12 (s,1H,NH).

Workup

  1. additiond 1.84)by portionwise addition
  2. stirringthe mixture was stirred at this temperature for a further hour
  3. customThe yellow solid was collected
  4. washwashed with water
  5. filtrationThe hot suspension was filtered
  6. washthe undissolved residue was washed with 200 ml of ether

Sources & evidence

ORD record
ord-dd6985d574384ab39555324c91108595
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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