Ammonium Chloride → (4-Amino-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone

HRID 926463Notes

Reaction equation

HRID 926463 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[C:11]([CH3:18])[CH:10]=2)=[O:8])=[CH:5][N:4]=[CH:3]1.[NH4+].[Cl-]>CC(C)=O.O.[Zn]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]([C:6]2[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=2)=[O:8])=[CH:10][C:11]=1[CH3:18]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86715615(1-Methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone2×

Product 1

HCID 86715616(4-Amino-3-methylphenyl)(1-methyl-1H-imidazol-5-yl)methanone

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Zn (2.66 g, 40.7 mmol) was added in 2 portions over a period of 2 minutes to a mixture of (1-methyl-1H-imidazol-5-yl)(3-methyl-4-nitrophenyl)methanone (2.0 g, 8.1 mmol, Intermediate 14: step b) and NH4Cl (2.18 g, 40.7 mmol) in acetone (18.5 mL) and water (8.2 mL) at 0° C. After stirring for 1 hour, the reaction mixture was filtered through Celite®, rinsing with EtOAc. Acetone and EtOAc were removed on a rotary evaporator and the aqueous layer was filtered and the solids dried under vacuum to provide the title compound.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. washrinsing with EtOAc
  3. customAcetone and EtOAc were removed on a rotary evaporator
  4. filtrationthe aqueous layer was filtered
  5. customthe solids dried under vacuum

Sources & evidence

ORD record
ord-3a2302d17aa64e8f99274dc693c84250
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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