Methanol → Methyl 4-amino-2-methylbenzoate

HRID 2235046Notes

Reaction equation

HRID 2235046 reaction equation
C([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[C:7]([CH3:14])[CH:6]=1)(=O)C.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:22]O>>[NH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([O:11][CH3:22])=[O:10])=[C:7]([CH3:14])[CH:6]=1

Participants

5

Reactant 4

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 27352244-Acetamido-2-methylbenzoic acid

Product 1

HCID 11672721Methyl 4-amino-2-methylbenzoate

Procedure

15 g (78 mmol) 4-acetamido-2-methyl-benzoic acid are suspended in 150 ml of methanol and combined with 11.2 ml (210 mmol) conc. sulphuric acid. The mixture is refluxed for three hours. Then excess methanol is eliminated in vacuo. The residue is poured onto ice water, made alkaline with 5 N sodium hydroxide solution and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated to dryness.

Workup

  1. temperatureThe mixture is refluxed for three hours
  2. additionThe residue is poured onto ice water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-cb5a61f3f9da4ea8af953365297d0001
Source dataset
uspto-grants-2010_05
Patent number
US07714000B2

Reaction notes

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