3-Methoxypropylamine → 3-methoxy-N-(3-methoxypropyl)-2-nitroaniline

HRID 1096625Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][O:14][CH2:15][CH2:16][CH2:17][NH2:18]>CN(C)C=O>[CH3:9][O:8][C:4]1[C:3]([N+:10]([O-:12])=[O:11])=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:18][CH2:17][CH2:16][CH2:15][O:14][CH3:13]

Participants

Conditions

Temperature: -15 °C

Procedure

Into a 25 mL round bottomed was added 1-fluoro-3-methoxy-2-nitrobenzene (500 mg, 2.92 mmol) and N,N-dimethylforamide (5.8 mL). The flask was cooled to −15° C. and 3-methoxypropylamine (313 mg, 3.5 mmol) in N,N-dimethylforamide (2.2 mL) was slowly added. The reaction was allowed to warm to room temperature overnight. Solvent was removed under vacuum and the residue was purified by column chromatography (20% ethylacetate:hexanes) to give 3-methoxy-N-(3-methoxypropyl)-2-nitroaniline (37A) as a yellow oil (560 mg, 80% yield). ESI-MS:m/z 241.3 (M+H)+.

Workup

temperatureto warm to room temperature overnight
customSolvent was removed under vacuum
customthe residue was purified by column chromatography (20% ethylacetate:hexanes)

Sources & evidence

ORD record: ord-d4e60868906449e39abb1a1a99a41b29
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138168B1

Reaction notes

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