N-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline → N1-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamine

HRID 1527734Notes

Reaction equation

HRID 1527734 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:11]=[CH:10][C:9]=2[N+:23]([O-])=O)=[CH:4][CH:3]=1>[Pt].[I-].[Zn+2].[I-].C(OCC)(=O)C>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]2[C:9]([NH2:23])=[CH:10][CH:11]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 90410173N-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline

Product 1

HCID 117607702N1-(4-Bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)benzene-1,2-diamineYield 83%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 9883512zinc(II)iodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a high pressure reactor were added N-(4-bromobenzyl)-5-((5-methylpyridin-2-yl)methoxy)-2-nitroaniline (78.4 g, 183 mmol), 5% Pt/C (35.7 g, 4.6 mmol), zinc iodide (5.84 g, 18.3 mmol) and ethyl acetate (1.5 L). The reactor was flushed with N2 and then stirred under an atmosphere of H2 (60 psi) for 18 h. The mixture was then filtered, washed with water (1 L), dried over magnesium sulfate and concentrated to dryness under reduced pressure to afford the title compound as an oil (60.4 g, 83%). MS (ESI): mass calcd. for C20H20BrN3O, 397.1; m/z found, 398.0 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.46-8.32 (m, 1H), 7.52-7.40 (m, 3H), 7.34 (d, J=8.0, 1H), 7.25-7.19 (m, 2H), 6.64 (d, J=8.1, 1H), 6.30-6.21 (m, 2H), 5.06 (s, 2H), 4.24 (s, 2H), 2.75 (bs, 2H), 2.32 (s, 3H).

Workup

  1. customThe reactor was flushed with N2
  2. filtrationThe mixture was then filtered
  3. washwashed with water (1 L)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7f9b5129b3974f3190ba21ae9052d33e
Source dataset
uspto-grants-2015_07
Patent number
US09089569B2

Reaction notes

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