Ammonia → HCID 19027047, compound

HRID 1032931Notes

Reaction equation

HRID 1032931 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13]([C:15](OCC)=[O:16])=[O:14])=[C:4]([N+:20]([O-:22])=O)[CH:3]=1.CN(C)C=O.N>O1CCCC1.[Pd]>[OH:22][N:20]1[C:4]2[CH:3]=[CH:2][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]=2[NH:12][C:13](=[O:14])[C:15]1=[O:16]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 19027046HCID 19027046, compound

Product 1

HCID 19027047HCID 19027047, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 0.5 g (1.36 mmol) 4-bromo-1-ethoxalylamino-2-nitronaphthalene in 30 ml tetrahydrofuran was added 10 ml dimethylformamide and 0.7 ml 25% aqueous ammonia. The mixture was hydrogenated at atm. pressure by using 50 mg 5% Pd-C as a catalyst. The precipitated product was filtered off and washed with tetrahydrofuran. The filter cake was washed several times with 5% aqueous potassium hydroxide. Acidification of the filtrate with 4N hydrochloric acid and recrystallization (dimethylformamide-water) of the precipitated product gave 0.2 g (65%) 4-hydroxy-benzo[f]quinoxaline-2,3(1H,4H)-dione. M.p. 270° C. decomp. 1H-N (1H, broad s), 8.6 (1H, m), 7.7 (5H, m). MS (m/e): 228 (M+, 90%).

Workup

  1. filtrationThe precipitated product was filtered off
  2. washwashed with tetrahydrofuran
  3. washThe filter cake was washed several times with 5% aqueous potassium hydroxide
  4. customAcidification of the filtrate with 4N hydrochloric acid and recrystallization (dimethylformamide-water) of the precipitated product

Sources & evidence

ORD record
ord-2545be20fc6d4e43826b48079cf8aa69
Source dataset
uspto-grants-1994_05
Patent number
US05308845

Reaction notes

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