Ethyl Acetate → 2-{2-[3-(1H-Indol-3-yl)-propylamino]-ethoxy}-6-nitro-phenylamine

HRID 1858360Notes

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].[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][CH2:26][NH2:27])=[CH:16]1.C(OCC)(=O)C>CS(C)=O>[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH2:24][CH2:25][CH2:26][NH:27][CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=2[NH2:14])=[CH:16]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 2-(2-chloro-ethoxy)-6-nitro-phenylamine (4.1 g, 19 mmol) and 3-(1H-indol-3-yl)-propylamine (7.1 g, 40.8 mmol) in anhydrous dimethylsulfoxide (50 ml) was heated at 60° C. for 12 hours. Ethyl acetate (200 ml) was added and the mixture was washed with saturated sodium bicarbonate (3×200 ml) and brine (200 ml). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude product. Purification by chromatography (ethyl acetate:hexanes:2N ammonia methanol=25:25:1) afforded 4.6 g (68.9%) of the product as a yellowish red viscous oil; MS EI m/e 354 (M+).

Workup

washthe mixture was washed with saturated sodium bicarbonate (3×200 ml) and brine (200 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude product
customPurification by chromatography (ethyl acetate:hexanes:2N ammonia methanol=25:25:1)

Sources & evidence

ORD record: ord-015e055b6605429cbc79dda51ff256a5
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150533

Reaction notes

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