Diisopropylethylamine → N1-(3-bromobenzyl)-4-(quinolin-2-ylmethoxy)benzene-1,2-diamine

HRID 1776709Notes

Reaction equation

HRID 1776709 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:9][C:8]=1[N+:25]([O-])=O.CCN(C(C)C)C(C)C>C1COCC1.[Pt]>[Br:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[CH2:5][NH:6][C:7]1[C:8]([NH2:25])=[CH:9][C:10]([O:13][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 90414456HCID 90414456, compound

Product 1

HCID 90414557N1-(3-bromobenzyl)-4-(quinolin-2-ylmethoxy)benzene-1,2-diamineYield 58.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-bromobenzyl)-2-nitro-4-(quinolin-2-ylmethoxy)aniline (5.9 g, 13 mmol) in THF (200 mL) was added DIPEA (1.1 mL, 6.4 mmol) followed by 5% platinum on carbon (0.4 g, 1.9 mmol). The reaction vessel was evacuated and placed under 1 atmosphere of H2 atmosphere for 23 h. The mixture was then flushed with N2 and filtered through a pad of Celite. The Celite was then rinsed with additional THF and the filtrate was concentrated to dryness. The resulting residue was purified using FCC to provide 3.3 g of the title compound as a tan solid. MS (ESI): mass calcd. for C23H20BrN3O, 434.33; m/z found 435.0 [M+H]+.

Workup

  1. customThe reaction vessel was evacuated
  2. customThe mixture was then flushed with N2
  3. filtrationfiltered through a pad of Celite
  4. washThe Celite was then rinsed with additional THF
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-084bab9e90004607ae3415f669da98c4
Source dataset
uspto-grants-2016_02
Patent number
US09265770B2

Reaction notes

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