Water → Methyl 2-[(3-chloropropyl)amino]-4-methoxy-3-nitrobenzoate

HRID 1398958Notes

Reaction equation

HRID 1398958 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([O:18][CH3:19])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[C:20](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C=O>[Cl:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([O:18][CH3:19])[CH:12]=[CH:11][C:7]=1[C:8]([O:10][CH3:20])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 687394202-[(3-Chloropropyl)amino]-4-methoxy-3-nitrobenzoic acid

Product 1

HCID 68736083Methyl 2-[(3-chloropropyl)amino]-4-methoxy-3-nitrobenzoateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-[(3-chloropropyl)amino]-4-methoxy-3-nitrobenzoic acid (1.77 g, 6.13 mmol) and potassium carbonate (847 mg, 6.13 mmol) in N,N-dimethylformamide (18 mL) was added iodomethane (0.38 mL, 6.10 mmol) at room temperature. After stirring at room temperature for 14 hr, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water (×5) and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound (1.60 g, 5.29 mmol, 86%) as a yellow amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water (×5) and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-1df10b66024a4577bfc797b5bfa56918
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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