Methanol → 3-Amino-2-methylbenzoic acid methyl ester

HRID 2208723Notes

Reaction equation

HRID 2208723 reaction equation
C[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[NH2:12].OS(O)(=O)=O.[CH3:18]O>>[NH2:12][C:3]1[C:4]([CH3:11])=[C:5]([CH:9]=[CH:10][CH:2]=1)[C:6]([O:8][CH3:18])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22754770HCID 22754770, compound

Product 1

HCID 38010253-Amino-2-methylbenzoic acid methyl esterYield 91%

Conditions

Temperature
70 °C

Procedure

To stirred solution of methyl 3-amino-2-methylbenzoic acid (5 g, 33.1 mmol) in methanol (50 mL), was added conc. H2SO4 (5 mL) at 0° C. and the mixture was heated at 70° C. for 22 h. On completion, methanol was removed under reduced pressure, and then sat. sodium bicarbonate solution was added and the product extracted with 10% MeOH/DCM. Combined organic layers were dried, concentrated to yield methyl 3-amino-2-methylbenzoate (5 g, 91%).

Workup

  1. customOn completion, methanol was removed under reduced pressure
  2. additionsat. sodium bicarbonate solution was added
  3. extractionthe product extracted with 10% MeOH/DCM
  4. customCombined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6255ec5fb7dc493c926ee410e2ec2e5c
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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