Reaction equation
ClCC[O:4]C1C=CC([NH2:11])=CC=1.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1.O.O.Cl[Sn]Cl>C(O)C>[NH4+:11].[OH-:4].[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1Participants
Conditions
- Temperature
- 70 °C
Procedure
4-(2-Chloro-ethoxy)-phenylamine can be synthesized by the following procedure. A suspension of 1-(2-chloro-ethoxy)-4-nitro-benzene (1.5 mmol) (from Example 1c) and SnCl2.2H2O (5.9 mmol) in absolute ethanol (120 mL) is heated at 70° C. for 2 h. The solvent is removed under vacuum and the residue is dissolved in 5% NaOH and extracted with EtOAc (3×50 mL). The organic layer is washed with 5% NaOH (1×50 mL), water (1×50 mL), brine, and dried over Na2SO4 and reduced to dryness. The dark crude residue is purified by silica chromatography using a mixture of DCM:MeOH:NH4OH=9:1:0.1 to isolate 4-(2-chloro-ethoxy)-phenylamine (90%) which is converted in the hydrochloride salt by treatment with HCl (1 eq of a 4N solution in dioxane). 1HNMR (400 MHz, CD3OD) δ 7.35-7.33 (m, 2H), 7.16-7.05 (m, 2H), 4.38 (m, 2H), 3.87 (m, 2H). MS (m/z) (M+1)+ 173.1.
Workup
- customThe solvent is removed under vacuum
- dissolutionthe residue is dissolved in 5% NaOH
- extractionextracted with EtOAc (3×50 mL)
- washThe organic layer is washed with 5% NaOH (1×50 mL), water (1×50 mL), brine
- dry with materialdried over Na2SO4
- customThe dark crude residue is purified by silica chromatography
- additiona mixture of DCM
Sources & evidence
- ORD record
- ord-1ac332e6bb0141e983e8ee02ce57dc83
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563894B2
Linked notes
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