Dimethylformamide → HCID 53693012, compound

HRID 1819379Notes

Reaction equation

HRID 1819379 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=C(N)[C:5]=1[Cl:11].[CH3:13][N:14]([CH:16]=O)[CH3:15].C(=O)([O-])[O-].[K+].[K+].CI>O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:16]([N:14]([CH3:13])[CH3:15])[C:5]=1[Cl:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15132848Methyl 3-amino-2-chlorobenzoate

Product 1

HCID 53693012HCID 53693012, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-3-amino-benzoic acid methyl ester (1.20 g, 6.47 mmol) was placed in a round bottomed flask with DMF (5 mL), Potassium carbonate (1.97 g, 14.2 mmol) and methyl iodide (0.89 mL, 14.22 mmol) were added. A reflux condenser was fitted and the reaction was heated to 60° C. for 12 h. The reaction was cooled to rt, diluted with water (20 mL) and extracted with ethyl acetate (3×20 mL). The organics were dried (MgSO4), concentrated, then purified by column chromatography using hexanes/ethyl acetate (1:1) to afford 2-chloro-3-dimethylamino-benzoic acid methyl ester (1.04 g, 75%)

Workup

  1. additionwere added
  2. customA reflux condenser was fitted
  3. temperatureThe reaction was cooled to rt
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe organics were dried (MgSO4)
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-cfa8fe73ef764814ae4461a519813d40
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

Loading…