HCID 4338554, compound → HCID 3624964, compound

HRID 1757802Notes

Reaction equation

HRID 1757802 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].C(OCC)(=O)C>[NH2:1][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:29])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 4338554HCID 4338554, compound

Product 1

HCID 3624964HCID 3624964, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.5 g of N-(3-nitrophenyl)octadecanamide and 0.6 g of 10% palladium on carbon in 100 ml of ethyl acetate was shaken under an initialhydrogen pressure of 52 psi until uptake ceased after 23 hours. The catalyst was removed by filtration and the filtrate was concentrated at reduced pressure to a solid which was recrystallized from methanol-water to give 4.6 g (90% yield, mp 98°-102°) of N-(3-aminophenyl)octadecanamide.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated at reduced pressure to a solid which
  3. customwas recrystallized from methanol-water

Sources & evidence

ORD record
ord-06183f5020be467fab50f1b9ea7b7b54
Source dataset
uspto-grants-1995_08
Patent number
US05446189

Reaction notes

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