Hydrochloric Acid → HCID 19875853, compound

HRID 1886365Notes

Reaction equation

HRID 1886365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([N:22]3[CH:26]=[N:25][CH:24]=[N:23]3)[CH:19]([CH3:21])[CH3:20])=[CH:14][C:13]=2[N+:27]([O-])=O)=[O:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.[K].Cl>CC(O)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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]=[N:25][CH:24]=[N:23]2)[CH:19]([CH3:21])[CH3:20])=[CH:16][CH:17]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 5462222PotassiumHCID 19875859HCID 19875859, compound

Product 1

HCID 19875853HCID 19875853, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a stirred mixture of 11 parts of 4-chloro-N-[4-[2-methyl-1-(1H-1,2,4-triazol-1-yl)propyl]-2-nitrophenyl]benzeneacetamide and 49 parts of pyridine were added 3.6 parts of 2-methyl-2-propanol, potassium salt under a nirogen atmosphere. After stirring for 1 hour at room temperature, the reaction mixture was poured into ice-water. The whole was neutralized with HCl 3N and the product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2). The eluent of the desired fraction was evaporated, yielding 6.6 parts (61.8%) of 3-(4-chlorophenyl)-6-[2-methyl1-(1H-1,2,4-triazol-1-yl)propyl]-2(1H)-quinoxalinone, N4 -oxide (comp. 221).

Workup

  1. extractionthe product was extracted with dichloromethane
  2. customThe extract was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 98:2)
  6. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-28ab2720c95c426aaaf4b47ec9fafa23
Source dataset
uspto-grants-1992_09
Patent number
US05151421

Reaction notes

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