5-Nitronaphthalene-1,4-dione → HCID 22164858, compound

HRID 1032688Notes

Reaction equation

HRID 1032688 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-:3])=[O:2].[CH:16]([N:18]1[CH:27](C(O)=O)[CH:26]([CH3:31])[CH:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH2:24]2)[CH2:19]1)=O>C(OC(=O)C)(=O)C>[CH3:31][CH:26]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][N:18]2[CH:16]=[C:7]3[C:8]([C:9](=[O:14])[C:10]4[CH:11]=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=4[C:6]3=[O:15])=[C:27]12

Participants

4

Reactant 2

HCID 123364025-Nitronaphthalene-1,4-dioneHCID 86744234HCID 86744234, compound

Product 1

HCID 22164858HCID 22164858, compoundYield 138.9%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 5-nitro-1,4-naphthoquinone (4.7 g) and N-formyl-4-methyl-3-tetrahydroisoquinolinecarboxylic acid (2.4 g) suspended in acetic anhydride (15 ml) was stirred and heated at 70°-75° for 21/2 hours. The mixture was cooled and the solid formed was collected by filtration, washed with acetic anhydride, then with ether and finally dried to give the title compound (5.4 g) as a yellow crystalline solid. N.m.r. in DMSOd6 (ppm) δ 1.49(14-CH3);4.88(14-H); 5.37, 5.47(5-CH2); 8.39(10-H). U.v. λmax 246 nm, E11 481; 376 nm, E11 83.

Workup

  1. temperatureheated at 70°-75° for 21/2 hours
  2. temperatureThe mixture was cooled
  3. customthe solid formed
  4. filtrationwas collected by filtration
  5. washwashed with acetic anhydride
  6. dry with materialwith ether and finally dried

Sources & evidence

ORD record
ord-c49d40de718d427190996ee3908370bb
Source dataset
uspto-grants-1990_09
Patent number
US04959371

Reaction notes

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