4-Nitrophenyl tetradecyl ether → p-(n-Tetradecyloxy)phenylamine

HRID 247990Notes

Reaction equation

HRID 247990 reaction equation
[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C(O)C.C(OCC)(=O)C.[Pd]>[CH2:1]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 1

HCID 103370514-Nitrophenyl tetradecyl ether

Product 1

HCID 191002p-(n-Tetradecyloxy)phenylamineYield 94.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 30 g of product from Example 81 in 150 ml of ethyl alcohol and 20 ml of ethyl acetate is treated with 2 g of 10% palladium/carbon in a Parr Hydrogenator for 18 hours. The reaction solution is filtered and concentrated in vacuo. The residue is recrystallized from hexane to give 25.7 g of the desired product as a white solid.

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-4f774d62cf354237a48ef823dcaa5de5
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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