HCID 19389002, compound → HCID 19389092, compound

HRID 1110300Notes

Reaction equation

HRID 1110300 reaction equation
[O:1]=[C:2]([O:12][C:13]1[CH:14]=[C:15]([N+:31]([O-])=O)[CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[H][H]>[Pd].C(OCC)(=O)C.C1COCC1>[O:1]=[C:2]([O:12][C:13]1[CH:14]=[C:15]([NH2:31])[CH:16]=[CH:17][C:18]=1[O:19][C:20](=[O:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 2

HCID 19389002HCID 19389002, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19389092HCID 19389092, compoundYield 92.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.9 g of 3,4-bis[(1-oxodecyl)oxy]nitrobenzene and 0.5 g of 10% palladium on carbon in 50 ml of ethyl acetate and 10 ml of THF was stirred in a hydrogen atmosphere at room temperature for 5 hours when uptake ceased. The catalyst was removed by filtration and the filtrate was concentrated to an oil which was crystallized from ethyl acetate-hexane to give 2.5 g (92% yield, mp 44°-46°) of 3,4-bis[(1-oxodecyl)oxy]benzenamine.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to an oil which
  3. customwas crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ecdab35609a84acfa65e0dbe42bd2aa7
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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