Hydrochloric Acid → 3-benzoyl-6-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2(1H)-quinoxalinone

HRID 1086216Notes

Reaction equation

HRID 1086216 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])[CH2:18][C:19](=[O:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:12]([N+:28]([O-])=O)[CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Cl>O>[C:19]([C:18]1[C:17](=[O:27])[NH:16][C:13]2[C:12]([N:28]=1)=[CH:11][C:10]([CH:6]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[CH:7]([CH3:9])[CH3:8])=[CH:15][CH:14]=2)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 19875839N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]-beta-oxobenzenepropanamide

Product 1

HCID 198758423-benzoyl-6-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2(1H)-quinoxalinoneYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7 parts of N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]-β-oxobenzenepropanamide, 7.03 parts of potassium carbonate and 70 parts of water was stirred for 1.5 hours at reflux temperature. After cooling, the whole was treated with a hydrochloric acid solution 3N to pH 7. The product was extracted with dichloromethane (3×104 parts). The combined extracts were dried, filtered and evaporated. The residue was taken up in ethanol. The product was filtered off and dried, yielding 5.1 parts (73.0%) of 3-benzoyl-6-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2(1H)-quinoxalinone, N4 -oxide monohydrate; mp. 210.0° C. (comp. 154).

Workup

  1. temperatureat reflux temperature
  2. temperatureAfter cooling
  3. extractionThe product was extracted with dichloromethane (3×104 parts)
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. customevaporated
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-249d0e1e07c64a08bff90b38b88fe8a7
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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