Sodium Hydroxide → 4-[2-(Pyridin-2-yloxy)ethoxy]aniline

Reaction equation

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

Participants

Procedure

2-[2-(4-Nitrophenoxy)ethoxy]pyridine (100 mg, 0.38 mmol) and tin (II) chloride dihydrate (433 mg, 1.92 mmol) were dissolved in ethanol (1.5 mL) and refluxed under nitrogen for 18 h. The reaction mixture was basified to pH 12 with 3M aqueous sodium hydroxide solution. The reaction mixture was stirred for 1 h and then filtered through Celite. The reaction mixture was concentrated in vacuo and the aqueous layer was separated and extracted with CH2Cl2 (5×). The combined organic extracts were concentrated in vacuo to give 4-[2-(pyridin-2-yloxy)ethoxy]aniline as a purple glassy solid. 1H NMR (d6-DMSO, 400 MHz): δ 8.16 (ddd, J=5.2, 2.0, 0.8 Hz, 1H), 7.71 (ddd, J=9.2, 7.2, 2.0 Hz, 1H), 6.99 (ddd, J=7.2, 5.2, 1.0 Hz, 1H), 6.85 (ddd, J=8.4, 0.8, 0.8 Hz, 1H), 6.68 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 6.50 (ddd, J=5.6, 3.6, 3.6 Hz, 2H), 4.62 (brs, 2H), 4.50 (m, 2H), 4.15 (m, 2H).