Nitric Acid → HCID 15066354, compound

HRID 1165808Notes

Reaction equation

HRID 1165808 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:1]([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([N+:27]([O-:29])=[O:28])=[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

4

Reactant 2

HCID 944Nitric Acid2×HCID 15066353HCID 15066353, compound

Product 1

HCID 15066354HCID 15066354, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1,2-diethoxalylaminonaphthalene (10.8 g, 0.03 mol) in 150 ml of acetic acid was treated dropwise with nitric acid (1.24 ml, 0.03 mol, d 1.52) and stirred over night at room temperature. Then an additional amount of nitric acid (2.0 ml, d 1.52) was added dropwise and the mixture was stirred for 17 h at room temperature. The mixture was poured into 200 ml of ice/water and the resulting precipitate was isolated by filtration and washed with water, a small amount of cold ethanol and ether affording 3.3 g (27%) of pure product, m.p. 183.0-184.0° C.

Workup

  1. stirringthe mixture was stirred for 17 h at room temperature
  2. customthe resulting precipitate was isolated by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-5a4772b4585f4e3bbc03d94d02eb59ac
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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