Sulfuric Acid → HCID 19875863, compound

HRID 1086219Notes

Reaction equation

HRID 1086219 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([N:22]3[CH:26]=[CH:25][N:24]=[CH:23]3)[CH:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[N+:27]([O-])=O)=[O:10])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].S(=O)(=O)(O)O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:10])[NH:11][C:12]3[C:13]([N:27]=2)=[CH:14][C:15]([CH:18]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 19875875HCID 19875875, compound

Product 1

HCID 19875863HCID 19875863, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 14.5 parts of 3-fluoro-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2-nitrophenyl]benzeneacetamide in 49 parts of pyridine and 10 parts of a potassium hydroxide solution 20% was stirred for 1 hour at 85° C. The reaction mixture was poured into crushed ice and neutralized with a sulfuric acid solution 2N. After evaporation, the residue was purified by column chromatography over silica gel using a mixture of dichloromethane, methanol and ammonium hydroxide (95:5:0.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of dichloromethane and 2,2'-oxybispropane. The product was filtered off and dried, yielding 4.3 parts (67.6%) of 3-(3-fluorophenyl)-6-[1-(1H-imidazol-1-yl)-2-methylpropyl]-2(1H)-quinoxalinone, N4 -oxide; mp. 212.9° C. (comp. 166).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. customAfter evaporation
  4. customthe residue was purified by column chromatography over silica gel using
  5. additiona mixture of dichloromethane, methanol and ammonium hydroxide (95:5:0.5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated
  8. customThe residue was crystallized from a mixture of dichloromethane and 2,2'-oxybispropane
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-a844522d0c1b46839645834cd959599b
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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