Potassium Nitrate → HCID 86745375, compound

HRID 1032938Notes

Reaction equation

HRID 1032938 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[C:6]([NH:13][C:14]1[CH:15]=[C:16]2[C:27](=[O:28])[O:26][C:24](=[O:25])[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([CH:23]=1)[C:17]2=3)([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7]>S(=O)(=O)(O)O>[C:6]([NH:13][C:14]1[CH:15]=[C:16]2[C:27](=[O:28])[O:26][C:24](=[O:25])[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:23]=1[N+:1]([O-:4])=[O:2])[C:17]2=3)([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 86745376HCID 86745376, compound

Product 1

HCID 86745375HCID 86745375, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Powdered potassium nitrate (0.51 g, 5 mmol) was added to a stirred solution of 3-ethoxalylamino-1,8-naphthalenedicarboxylic anhydride (1.57 g, 5 mmol) in 15 ml of conc. sulfuric acid at 0° C. Stirring was continued for 2 h at the same temperature, then the reaction mixture was poured into 150 ml of ice-water. The separated yellow solid was isolated by filtration and washed with water, ethanol and ether. Trituration with a small amount of ethyl acetate afforded 1.38 g (77%) of the title compound. M.p. 221°-222° C.; 1H-NMR (CDCl3 +DMSO-d6): 1.43 (t,J ™7Hz, 3H, CH3), 4.37 (q,J =7Hz, 2H, CH2), 7.70-8.60 (m, 3H, ArH), 8.82 (s, 1H, H-2), 11.3 (broad s, 1H, NH).

Workup

  1. customThe separated yellow solid was isolated by filtration
  2. washwashed with water, ethanol and ether

Sources & evidence

ORD record
ord-79d6659946334e1cac65030c2de23807
Source dataset
uspto-grants-1994_05
Patent number
US05308845

Reaction notes

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