Hydrochloric Acid → HCID 14722565, compound

HRID 1494648Notes

Reaction equation

HRID 1494648 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:11]([Cl:12])=[CH:10][C:9]([C:13]#[N:14])=[CH:8][C:7]=1[Cl:15])=[O:4].CC(O)C.Cl.[H][H]>[Pd].CO>[NH2:14][CH2:13][C:9]1[CH:8]=[C:7]([Cl:15])[C:6]([NH:5][C:3](=[O:4])[CH2:2][Cl:1])=[C:11]([Cl:12])[CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 147225642-chloro-N-(2,6-dichloro-4-cyanophenyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 14722565HCID 14722565, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 10.5 parts of 2-chloro-N-(2,6dichloro-4-cyanophenyl) acetamide, 22 parts of 2-propanol, saturated with hydrogen chloride and 200 parts of methanol was hydrogenated at normal pressure and at room temperature with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was taken up in water and treated with a sodium hydroxide solution 50%. The product was extracted twice with dichloromethane. The combined extracts were dried, filtered and evaporated, yielding 10.7 parts (100%) of N-[4-(aminomethyl)-2,6-dichlorophenyl]-2-chloroacetamide as a residue (int. 100).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. additiontreated with a sodium hydroxide solution 50%
  4. extractionThe product was extracted twice with dichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dd68f311d57a428eb965e7053a3a756f
Source dataset
uspto-grants-1991_06
Patent number
US05026853

Reaction notes

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