Ethylamine → N-ethyl-4-nitro-benzene-1,2-diamine

HRID 1391535Notes

Reaction equation

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

Participants

Reactant 2

HCID 6341Ethylamine

HCID 677852-Fluoro-5-nitroaniline

Product 1

HCID 4613404N-ethyl-4-nitro-benzene-1,2-diamineYield 72%

Procedure

2-fluoro-5-nitroaniline (5 g, 32 mmol) and a solution of ethyl amine (32 ml, 2M in THF) were coupled according to the procedure of intermediate example one part A to give the title compound as a dark red solid 4.16 g, 72%). 1H NMR (300 MHz, d6-DMSO) δ7.51 (dd, J=8.7 and 2.7 Hz, 1H), 7.38 (d, J=2.7 Hz, 1H), 6.44 (d, J=8.7 Hz, 1H), 5.86 (t, J=4.6 Hz, 1H), 5.15 (s, 2H), 3.20 (m, 2H), 1.21 (t, J=7.2 Hz, 3H).

Sources & evidence

ORD record: ord-21ef47374b4747ddaf6c50780fb33cfc
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338959B2

Reaction notes

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