HCID 15066352, compound → HCID 178516982, compound

HRID 1165806Notes

Reaction equation

HRID 1165806 reaction equation
C([NH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([Br:19])=[CH:11][C:10]=1[NH:20][C:21]([C:23]([O:25]CC)=O)=[O:22])(C(OCC)=O)=O>Cl.C(O)(=O)C>[Br:19][C:12]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=2[C:9]2[N:8]=[C:23]([OH:25])[C:21]([OH:22])=[N:20][C:10]=2[CH:11]=1

Participants

4

Reactant 1

HCID 15066352HCID 15066352, compound

Product 1

HCID 178516982HCID 178516982, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,0 g (4,6 mmol) 1,2-diethoxalylamino-4-bromonaphthalene in 50 ml 2N hydrochloric acid and 25 ml acetic acid was refluxed for 1,5 h. After cooling to 25° C., the precipitate was filtered off. The crude product was recrystallized (dimethylformamide-water) to give 1,2 g ( 90%) of pure 6-bromo-2,3-dihydroxybenzo(f)quinoxaline, m.p. > 300° C.1H NMR (DMSO-d6): 8,8 (1H,m), 8,3 (1H,m), 7,87 (1H,s), 7,7 (2H,m).

Workup

  1. temperaturewas refluxed for 1,5 h
  2. filtrationthe precipitate was filtered off
  3. customThe crude product was recrystallized (dimethylformamide-water)

Sources & evidence

ORD record
ord-f1375c882c40426e9e67cf25fb7ba087
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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