Hydrochloric Acid → 3-Amino-2-methylbenzoic acid methyl ester

HRID 476529

Reaction equation

HRID 476529 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO.[Fe]>[NH2:12][C:11]1[C:2]([CH3:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 38010253-Amino-2-methylbenzoic acid methyl esterYield 82.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

40 g of methyl 2-methyl-3-nitrobenzoate was dissolved in 120 ml of methanol, and 157 g of concentrated hydrochloric acid was added thereto. Then, 36.8 g of iron powder was gradually added while maintaining the mixture at a temperature of not higher than 60° C. The mixture was stirred at room temperature for 4 hours and then poured into 1 liter of ice water. The solution was neutralized with sodium carbonate and extracted with chloroform (after filtering off insolubles). The extract was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 27.8 g of the desired product as an oily substance.

Workup

  1. extractionextracted with chloroform (after filtering off insolubles)
  2. washThe extract was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-2cd6a3df76fe4a0d85dd76b53090eeaa
Source dataset
uspto-grants-1989_12
Patent number
US04885022

Linked notes

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