HCID 19873419, compound → HCID 19873378, compound

HRID 466359Notes

Reaction equation

HRID 466359 reaction equation
[CH2:1]([N:3]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)[CH3:2].[H][H]>CO.[Pd]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([N:3]([CH2:1][CH3:2])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 19873419HCID 19873419, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19873378HCID 19873378, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-Ethyl-N-heptyl-4-nitrophenylacetamide (Preparation 18) (7.5 g) is hydrogenated on the Parr hydrogenator in two portions; i.e., 3.75 g in 150 ml methanol plus 0.4 g of 10% Pd/C catalyst at an initial hydrogen pressure of 50 psi. The hydrogen uptake ceases after 15 min; after 15 min more, the mixture is filtered through Celite. The filtrates of both runs are pooled and concentrated in vacuo. The residue is dissolved in 20 ml of EtOH, 200 ml of Et2O is added and the mixture treated with 12.0 ml of ca. 2.8M ethereal HCl with a resulting precipitate. This precipitate is collected and washed with ether to give the title compound; m.p. 172°-174° C.

Workup

  1. filtrationthe mixture is filtered through Celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue is dissolved in 20 ml of EtOH
  4. addition200 ml of Et2O is added
  5. additionthe mixture treated with 12.0 ml of ca. 2.8M ethereal HCl with a resulting precipitate
  6. customThis precipitate is collected
  7. washwashed with ether

Sources & evidence

ORD record
ord-98dc0a8467424372bb94a03cf9397e72
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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