Sodium Carbonate → 4-((2-Amino-4-(quinolin-2-ylmethoxy)phenylamino)methyl)benzonitrile

HRID 2178446Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=[CH:6][C:5]=1[NH:22][CH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1)([O-])=O.O.O.Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>CCOC(C)=O>[NH2:1][C:4]1[CH:9]=[C:8]([O:10][CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)[CH:7]=[CH:6][C:5]=1[NH:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]#[N:29])=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-(((2-nitro-4-(quinolin-2-ylmethoxy)phenyl)amino)methyl)benzonitrile (2.8 g, 6.7 mmol) in EtOAc (100 mL) was added SnCl2.2H2O (9.4 g, 42 mmol) and the mixture heated to 70° C. for 3 h. The mixture was then cooled to RT and basified to pH=8 by addition of 2 M Na2CO3 and stirred at RT. After 12 hours, the mixture was extracted with EtOAc and concentrated to dryness. The residue was then purified by FCC to afford 0.69 g of the title compound. MS (ESI): mass calcd. for C24H20N4O, 380.45; m/z found 381.2 [M+H]+.

Workup

extractionthe mixture was extracted with EtOAc
concentrationconcentrated to dryness
customThe residue was then purified by FCC

Sources & evidence

ORD record: ord-e75117be185a43f38b64571d3ce5e638
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067917B2

Reaction notes

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