Sodium Chloride → Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate

HRID 623280Notes

Reaction equation

HRID 623280 reaction equation
[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.[Cl-].[Na+]>CN(C=O)C>[CH3:13][O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([Cl:12])[CH:9]=[C:10]([CH3:11])[C:2]=1[NH2:1]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 116440442-Amino-5-chloro-3-methylbenzoic acid

Product 1

HCID 12744623Methyl 2-amino-5-chloro-3-methylbenzenecarboxylateYield 1,218.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 500 mL round-bottom flask, 0.2 mol of 2-amino-3-methyl-5-chlorobenzoic acid having the structural formula of IV-5, 300 mL of DMF and 2.0 grams of potassium carbonate were added, stirred at room temperature for 0.5 hour, dimethyl sulfate was dripped, reacted at 110° C. for 7 hours, and cooled to room temperature, poured into a saturated sodium chloride solution, extracted with acetate ethyl, dried over anhydrous sodium sulfate, filtered and the solvent was removed to obtain a crude product, 35.2 grams of 2-amino-3-methyl-5-chlorobenzoic acid methyl ester having a structural formula of VIII-3 was obtained by column chromatography, and the yield was 88.4%;

Workup

  1. customreacted at 110° C. for 7 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with acetate ethyl
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-238c723639fe4eacb68332442c26e1ea
Source dataset
uspto-grants-2016_04
Patent number
US09301529B2

Reaction notes

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