Benzylamine → 2-(2-Benzylamino-ethoxy)-6-nitro-phenylamine
Reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([NH:22][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH2:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
3
Conditions
- Temperature
- 600 °C
Procedure
A mixture of 2-(2-chloro-ethoxy)-6-nitro-phenylamine (1a, 3.0 g, 13.8 mmol) and benzylamine (9.0 g, 84.0 mmol) was heated neat at 100-1100° C. for 6 hr. The excess benzylamine was removed by distillation under vacuum (70-75° C./0.1 mm). The residue was poured into 1 N sodium hydroxide (300 mL) and extracted with ethyl acetate (2×, 300 mL). The combined organic layer was washed with water (2×, 300 mL) and brine (300 mL). The ethyl acetate layer was dried over anhydrous magnesium sulfate, filtered, and the solvent removed under vacuum to give 5.1 g of crude red oil. Purification by chromatography (500 g silica gel, ethyl acetate: 2 M NH3 in methanol, 20:1) afforded 3.54 g (89.3%) of a red semi-solid, mp 33-60° C.; MS EI m/e 287 (M+).
Workup
- customThe excess benzylamine was removed by distillation under vacuum (70-75° C./0.1 mm)
- additionThe residue was poured into 1 N sodium hydroxide (300 mL)
- extractionextracted with ethyl acetate (2×, 300 mL)
- washThe combined organic layer was washed with water (2×, 300 mL) and brine (300 mL)
- dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent removed under vacuum
- customto give 5.1 g of crude red oil
- customPurification by chromatography (500 g silica gel, ethyl acetate: 2 M NH3 in methanol, 20:1)
Sources & evidence
- ORD record
- ord-2316c8032bef4eb797694185061e82ad
- Source dataset
- uspto-grants-1999_11
- Patent number
- US05990144
Reaction notes
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