Methylamine → 2-Nitro-6-methylaminobenzonitrile

HRID 471624Notes

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[C:5]=1[C:6]#[N:7])([O-:3])=[O:2].[CH3:15]N>>[CH3:15][NH:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[C:6]#[N:7]

Participants

Reactant 2

HCID 6329Methylamine

HCID 520718Dinitrobenzonitrile

Product 1

HCID 127157712-Nitro-6-methylaminobenzonitrileYield 79%

Procedure

Prepared as in Example 90c from 2,6-dinitrobenzonitrile and methylamine to give 2-methylamino-6-nitrobenzonitrile (0.42 g, 79%). 1H NMR (400 MHz, DMSO-d6) δ 2.85 (d, J=5.2 Hz, 3H), 6.75 (d, J=4.8 Hz, NH), 7.16 (d, J=8.4 Hz, 1H), 7.45 (d, J=7.6 Hz, 1H), 7.64 (t, J=8.4 Hz, 1H).

Sources & evidence

ORD record: ord-84d30916d30d450a8563081529c44000
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633186B2

Reaction notes

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