3-(4-Methyl-imidazol-1-yl)-2-nitro-phenylamine → 3-(4-Methyl-imidazol-1-yl)-benzene-1,2-diamine

HRID 589485Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 3-(4-methyl-imidazol-1-yl)-2-nitro-phenylamine (CXXIX) in methanol was added with 5% Pd/C. The combination was stirred under a hydrogen filled balloon at 40° C. for 6 hours. The solution was then filtered through a pad of Celite. The filtrate was concentrated in vacuo to get 3-(4-methyl-imidazol-1-yl)-benzene-1,2-diamine (CXXX). 1H NMR (CDCl3, 400 MHz) δ ppm 2.17 (s, 3H), 6.54 (m, 1H), 6.80 (m, 1H), 6.97 (m, 1H), 7.28 (m, 1H), 7.56 (m, 1H).

Workup

filtrationThe solution was then filtered through a pad of Celite
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-4058852b2c2b429b8005016988ba39f4
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233104B2

Reaction notes

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