Methyl iodide → Methyl 4-chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoate

HRID 1398949Notes

Reaction equation

HRID 1398949 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][Cl:15])[C:3]=1[N+:16]([O-:18])=[O:17].CI.[C:21](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:21])=[O:7])=[C:4]([NH:11][CH2:12][CH2:13][CH2:14][Cl:15])[C:3]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 687361724-Chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoic acid

Product 1

HCID 68737379Methyl 4-chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-chloro-2-[(3-chloropropyl)amino]-3-nitrobenzoic acid (150 mg, 0.512 mmol), methyl iodide (0.0319 mL, 0.512 mmol) and potassium carbonate (70.8 mg, 0.512 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at room temperature for 12 h. After addition of ethyl acetate, the resultant mixture was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on NH silica gel eluting with a 5% ethyl acetate/n-hexane mixture to afford a yellow oil (141 mg, 0.459 mmol, 90%).

Workup

  1. washthe resultant mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on NH silica gel eluting with a 5% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-ca10df22104d40c29db6c322f0aa5b36
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…