N-Ethylaniline → HCID 67045409, compound

HRID 2367146Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[CH2:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12].[O-]CCCC.[Na+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[CH2:11]([N:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1)[CH3:12]

Participants

Conditions

Temperature: 110 °C

Procedure

1-Bromo 3-nitrobenzene (500 mg, 2.5 mmol) and N-ethylaniline (375 μL, 3.0 mmol) were dissolved in toluene (15 ml) and sodium butoxide (193 mg, 2.0 mmol), Xantphos (143 mg, 0.25 mmol) and tris (dibenzylideneacetone) dipalladium (57 mg, 0.06 mmol) were added. The reaction mixture was stirred at 110° C. for 16 hours. The mixture was filtered through celite and the filtrate was concentrated to give crude product, which was purified by column chromatography (9:1 hexanes-ethyl acetate) to give N-ethyl-3-nitro-N-phenylaniline as colorless oil (400 mg, 1.65 mmol, 67% yield). 1H NMR (400 MHz, CDCl3): 6.99-7.59 (m, 8H), 6.58-6.69 (m, 1H), 3.79 (q, 2H), 1.25 (t, 3H); MS (EI) for C14H14N2O2: 242 (MH+).

Workup

filtrationThe mixture was filtered through celite
concentrationthe filtrate was concentrated
customto give crude product, which
customwas purified by column chromatography (9:1 hexanes-ethyl acetate)

Sources & evidence

ORD record: ord-02475d839f7d479689daa2bd49937dc5
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697737B2

Reaction notes

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