[Cl:1][C:2]1[C:16]([N+:17]([O-])=O)=[CH:15][CH:14]=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.C([O-])=O.[NH4+]>C1(C)C=CC=CC=1.O.[Fe]>[Cl:1][C:2]1[C:3]([O:4][CH2:5][CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[CH:13][CH:14]=[CH:15][C:16]=1[NH2:17]4-(2-(2-chloro-3-nitrophenoxy)ethyl)morpholine (873 mg, 3.1 mmol) was dissolved in toluene (12 mL). Ammonium formate (866 mg, 13.7 mmol) was dissolved in H2O (12 mL) and added. Iron powder (<10 micron, 766 mg, 13.7 mmol) was added and the reaction was placed in a 120° C. oil bath. After 1.25 h, the solution was cooled to 23° C. and filtered over a pad of celite eluting with 10% MeOH/dichloromethane (250 mL). The filtrate was concentrated in vacuo and the residue was purified via flash column chromatography to give 2-chloro-3-(2-morpholinoethoxy)aniline (503 mg, 75%) as a golden oil.
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