Methyl iodide → HCID 67106353, compound

HRID 880407Notes

Reaction equation

HRID 880407 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10](=O)[CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)[CH:3]=1.B.[CH3:24]SC.NC1C=C(C)C=C(C)N=1.CI.[H-].[Na+]>C1COCC1.[Ni].CO>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][CH2:10][N:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=2)[CH3:24])=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 215072-Amino-4,6-dimethylpyridineHCID 24758Sodium hydrideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67106288HCID 67106288, compound

Product 1

HCID 67106353HCID 67106353, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

From 4-nitrophenol by etherification with bromoacetic acid in the presence of sodium hydride in THF, acid chloride formation with thionyl chloride and catalytic DMF and amide formation with 2-amino-4,6-dimethylpyridine in triethylamine and chloroform to give N-(4,6-dimethyl-pyridin-2-yl)-2-(4-nitro-phenoxy)-acetamide. The amide is the reduced with borane-dimethylsulfide in THF at reflux, the resulting amine methylated with methyl iodide in the presence of sodium hydride in THF, and finally catalytic hydrogenation over Raney nickel in methanol gives the required aniline.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-c3a3499071df4040a32eea9aacfa2e7a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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