HCID 11310838, compound → 4-Octylaniline

HRID 1802117Notes

Reaction equation

HRID 1802117 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][CH:5]=1)([O-])=O>[Pd].CO>[CH2:10]([C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 1

HCID 11310838HCID 11310838, compound

Product 1

HCID 853464-OctylanilineYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A MeOH (20 mL) solution of compound (E)-1-nitro-4-(oct-1-enyl)benzene (2.121 g, 9.0 mmol) and Pd—C (200 mg, 0.9 mmol) was stirred at r.t. for 2 h under hydrogen atmosphere. Then the mixture was filtered and the filtrate was evaporated to give product the title compound (1.586 g, 85%) as a pink liquid. 1H NMR (300 MHz, CDCl3) δ 6.962 (d, 2H), 6.636 (d, 2H), 3.487 (b, 2H), 2.484 (t, 2H), 1.581-1.467 (m, 2H), 1.291-1.166 (m, 10H), 0.874 (t, 3H).

Workup

  1. filtrationThen the mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-f1a6273cbc6a47cdb759c8317ecf3323
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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