Nitric Acid → HCID 15066355, compound

HRID 477764Notes

Reaction equation

HRID 477764 reaction equation
[C:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[NH:19][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2].[N+:27]([O-])([OH:29])=[O:28]>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[N+:27]([O-:29])=[O:28])[CH:12]=[CH:11][C:10]=1[NH:19][C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:21])([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 15066353HCID 15066353, 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.

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

Sources & evidence

ORD record
ord-4e0868c28f1245139c77b1db3476df48
Source dataset
uspto-grants-1989_12
Patent number
US04889855

Reaction notes

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