Methylamine → 3,4-Dimethoxy-N-methyl-5-nitrobenzamide

HRID 1920080Notes

Reaction equation

HRID 1920080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6](Cl)=[O:7].[CH3:17][NH2:18]>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[C:11]=1[O:12][CH3:13])[C:6]([NH:18][CH3:17])=[O:7]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 219286153,4-Dimethoxy-5-nitrobenzoyl chloride

Product 1

HCID 670370593,4-Dimethoxy-N-methyl-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3,4-dimethoxy-5-nitro-benzoyl chloride (0.50 g, 2.04 mmol) in dichloromethane (10 mL) at 0° C., was added dropwise methylamine (1.02 mL, 2.04 mmol, 2 M in THF). The reaction mixture was stirred at room temperature till all starting material disappeared, then diluted with dichloromethane and washed with water. The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated to dryness to leave a crude residue that was recrystallised from a dichloromethane/isopropanol mixture to afford 3,4-dimethoxy-N-methyl-5-nitro-benzamide, 0.44 g (89%).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customto leave a crude residue that
  6. customwas recrystallised from a dichloromethane/isopropanol mixture

Sources & evidence

ORD record
ord-85c55b25cb5847c89b50f1e962adf583
Source dataset
uspto-grants-2012_05
Patent number
US08168793B2

Reaction notes

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