Hydrochloric Acid → HCID 19816011, compound

HRID 2247892Notes

Reaction equation

HRID 2247892 reaction equation
[OH-:1].[K+].C([C:5]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[C:6]1[CH:11]=[CH:10][C:9](=[N:12][OH:13])[C:8]([C:14]([OH:16])=[O:15])=[CH:7]1)#N.[OH:23]O.Cl>O>[C:5]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:13])=[O:23])=[C:8]([CH:7]=1)[C:14]([OH:16])=[O:15])(=[O:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14797Potassium HydroxideHCID 86744959HCID 86744959, compound

Product 1

HCID 19816011HCID 19816011, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 16.2 parts of potassium hydroxide, 150 parts of water and 5.72 parts of intermediate 17, namely 3-(cyanophenylmethylene)-6-(hydroxyimino)-1,4-cyclohexadiene-1-carboxylic acid, was added a solution of 16.25 parts of hydrogen peroxide in 16 parts of water. After stirring for 1 hour at room temperature, the reaction mixture was acidified with HCl while cooling on ice. The product was extracted with dichloromethane and the extract was dried, filtered and evaporated. The residue was recrystallized from methylbenzene, yielding 3.7 parts (63.5%) of 5-benzoyl-2-nitrobenzoic acid; mp. 168.6° C. (interm. 18).

Workup

  1. temperaturewhile cooling on ice
  2. extractionThe product was extracted with dichloromethane
  3. customthe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was recrystallized from methylbenzene

Sources & evidence

ORD record
ord-b7a27218f97e4caea8f8e7b526e66128
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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