Hydrochloric Acid → HCID 21495611, compound

HRID 1731187Notes

Reaction equation

HRID 1731187 reaction equation
Cl.[CH3:2][C:3]1[C:17]([N+:18]([O-])=O)=[CH:16][CH:15]=[CH:14][C:4]=1[C:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)=[O:6].[H][H]>O.C(O)C.[Pd](Cl)Cl>[CH3:2][C:3]1[C:17]([NH2:18])=[CH:16][CH:15]=[CH:14][C:4]=1[C:5]([C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1)=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21495669HCID 21495669, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21495611HCID 21495611, compoundYield 58.7%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

38 ml of hydrochloric acid, 23 g of activated carbon and 12 ml of a solution of 20% palladium chloride in water were added to a solution of 114.7 g of 2-methyl-3-nitro-4'-fluorobenzophenone in 1 liter of ethanol and then a current of hydrogen was passed therethrough for 3 hours. The reaction mixture was filtered and the filter was rinsed with ethanol. The filtrate was concentrated until crystallization began and was iced and then vacuum filtered. The precipitate was empasted with ethanol and dried under reduced pressure to obtain 59.5 g of 2-methyl-3-amino-4'-fluorobenzophenone in the form of white crystals melting at 170° C. Evaporation of the mother liquor and treatment with isopropyl ether gave another 50.5 g of product for a total of 110 g. For analysis, a sample of the product was crystallized from an aqueous solution of 5% hydrochloric acid and melted at 170° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter was rinsed with ethanol
  3. concentrationThe filtrate was concentrated until crystallization
  4. filtrationvacuum filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-989b5eb8f2e1459f8580d37fc5c96d06
Source dataset
uspto-grants-1976_11
Patent number
US03995056

Reaction notes

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