Sodium Hydroxide → HCID 54021776, compound

HRID 1086222Notes

Reaction equation

HRID 1086222 reaction equation
[N:1]1([CH:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[C:11]([CH3:18])=[N:10]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Na+].[NH2:27]OS(O)(=O)=O>O>[NH2:27][N:13]1[C:14]2[C:9](=[CH:8][C:7]([CH:6]([N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[CH:16][CH:15]=2)[N:10]=[C:11]([CH3:18])[C:12]1=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 54249470HCID 54249470, compound

Product 1

HCID 54021776HCID 54021776, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5 parts of 6-[(1H-imidazol-1-yl)phenylmethyl]-3-methyl-2(1H)-quinoxalinone, 3.3 parts of sodium hydroxide and 30 parts of water was stirred for 1 hour at room temperature. 5 Parts of hydroxylamine-O-sulfonic acid were added and the reaction mixture was stirred for 4 hours at 20° C. The product was extracted with dichloromethane (3×65 parts). The combined extracts were dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane. The product was filtered off and dried, yielding 2 parts (38.2%) of 1-amino-6-[(1H-imidazol-1-yl)phenylmethyl]-3-methyl-2(1H)-quinoxalinone; mp. 192.8° C. (comp. 85).

Workup

  1. stirringthe reaction mixture was stirred for 4 hours at 20° C
  2. extractionThe product was extracted with dichloromethane (3×65 parts)
  3. customThe combined extracts were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel using
  7. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-ce594ca17059467982ca730749f5daa1
Source dataset
uspto-grants-1991_07
Patent number
US05028606

Reaction notes

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