2,5-Dimethylaniline → HCID 11042464, compound

HRID 2266980Notes

Reaction equation

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

Participants

Reactant 4

HCID 72592,5-Dimethylaniline

HCID 8909Butyl ether

HCID 121674-Chloroanisole

HCID 23676156Sodium t-butoxide

Product 1

HCID 11042464HCID 11042464, compoundYield 97%

Conditions

Temperature: 110 °C

Procedure

Following general procedure E, a mixture of 4-chloroanisole (123 μL, 1.0 mmol), 2,5-dimethylaniline (149 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 (220 mg, 97%), mp 40-41° C. 1H NMR (300 MHz, CDCl3) δ: 7.11 (m, 3H), 6.96 (m, 3H), 6.75 (d, J=7.5 Hz, 1H), 5.27 (s, 1H), 3.88 (s, 3H), 2.33 (s, 3H), 2.30 (s, 3H) ppm. 13C NMR (75 MHz, CDCl3) δ: 155.3, 143.5, 136.8, 136.7, 131.0, 122.7, 122.5, 121.1, 116.2, 115.0, 55.9, 21.7, 17.7 ppm. IR (neat, cm−1): 3400, 2921, 1579, 1511, 1463, 1292, 1241, 1037, 828, 800. Anal. Calcd. for C15H17NO: C, 79.26; H, 7.54. Found: C, 79.11; H, 7.59.

Workup

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

Sources & evidence

ORD record: ord-1050388f59824ca08f575614e3efdc39
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858784B2

Reaction notes

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