4-Methoxybenzyl alcohol → HCID 61709251, compound

HRID 1621781Notes

Reaction equation

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

Participants

Conditions

Temperature: 160 °C

Procedure

A solution of 4-amino-2-chloropyridine (Aldrich) (1.000 g, 7.78 mmol) in 4-methoxybenzyl alcohol (Fluka) (9.66 mL, 78 mmol) was treated with sodium hydroxide (J. T. Baker) (0.584 mL, 31.1 mmol) and tetrabutylammonium iodide (Aldrich) (0.287 g, 0.778 mmol). The resulting mixture was heated at 160° C. under N2 for 2 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 20% to 30% acetone in hexanes) to give the product as a white solid (1.32 g). m/z (ESI, +ve ion) 231.1 (M+H)+. 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=5.70 Hz, 1H); 7.38 (d, J=8.18 Hz, 2H); 6.91 (d, J=8.48 Hz, 2H); 6.22 (d, J=7.02 Hz, 1H); 5.99 (s, 1H); 5.27 (s, 2H); 4.04 (br. s., 2H); 3.82 (s, 3H).

Workup

customThe reaction mixture was partitioned between EtOAc and water
extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated
customThe crude product was purified by column chromatography (120 g, 20% to 30% acetone in hexanes)

Sources & evidence

ORD record: ord-b3c95e7b11b347cfa88fb84b097c2bb6
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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