Butyl ether → 4-ethoxy-N-(4-methoxyphenyl)aniline

HRID 2266979Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1)[CH3:11].CC([O-])(C)C.[Na+].O(CCCC)CCCC>>[CH2:10]([O:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[CH:15][CH:14]=1)[CH3:11]

Participants

Reactant 4

HCID 8909Butyl ether

HCID 90764-Ethoxyaniline

HCID 121674-Chloroanisole

HCID 23676156Sodium t-butoxide

Product 1

HCID 578574774-ethoxy-N-(4-methoxyphenyl)anilineYield 94.1%

Conditions

Temperature: 110 °C

Procedure

Following general procedure E, a mixture of 4-chloroanisole (123 μL, 1.0 mmol), 4-ethoxyaniline (154 μL, 1.2 mmol), NaOt-Bu (115 mg, 1.2 mmol), 10 (0.08 mg, 0.01 mol %), 1 (0.05 mg, 0.01 mol %), and Bu2O (1 mL) was heated to 110° C. for 1 h. The crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes) to provide the title compound as a white solid (229 mg, 94%), mp 73-75° C. 1H NMR (300 MHz, CDCl3) δ: 6.95 (m, 4H), 6.84 (m, 4H), 5.34 (s, 1H), 4.01 (q, J=7.0 Hz, 2H), 3.80 (s, 3H), 1.43 (t, J=7.0 Hz, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 154.4, 153.8, 138.2, 138.1, 119.8, 119.7, 115.7, 114.9, 64.1, 55.9, 15.3 ppm. IR (neat, cm−1): 3421, 2983, 2956, 1513, 1298, 1253, 1116, 1052, 1037, 814. Anal. Calcd. for C15H17NO2: C, 74.05; H, 7.04. Found: C, 73.95; H, 7.06.

Workup

customThe crude product was purified via the Biotage SP4 (silica-packed 25+M; 0-30% EtOAc/hexanes)

Sources & evidence

ORD record: ord-21891dfd3291423282bb6d8abf4c7deb
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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