Hydrochloric Acid → 5-Butyl-2-methylaniline

HRID 2417907Notes

Reaction equation

HRID 2417907 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][CH3:11])=[CH:4][C:3]=1[N+:13]([O-])=O.CC(O)C.Cl.[H][H]>[Pd].CO>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH2:13])[CH:4]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 3448470HCID 3448470, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 204469815-Butyl-2-methylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 34 parts of 1-(4-methyl-3-nitrophenyl)-1-butanone, 24 parts of 2-propanol saturated with hydrochloric acid and 400 parts of methanol is hydrogenated at normal pressure and at room temperature with 5 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. Water is added to the residue and the whole is alkalized with ammonium hydroxide. The product is extracted with 2,2'-oxybispropane. The extract is dried, filtered and evaporated, yielding 25.5 parts of 5-butyl-2-methylbenzenamine as a residue.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. additionWater is added to the residue
  4. extractionThe product is extracted with 2,2'-oxybispropane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-4e3d16c244f149de84a541f797a55302
Source dataset
uspto-grants-1984_09
Patent number
US04471117

Reaction notes

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