Methanol → HCID 67404328, compound

HRID 906128Notes

Reaction equation

HRID 906128 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13].S(=O)(=O)(O)O.[CH3:20]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:20])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 53406085HCID 53406085, compound

Product 1

HCID 67404328HCID 67404328, compoundYield 75%

Conditions

Temperature
60 °C

Procedure

A mixture of 4-amino-2-methyl-3-nitrobenzoic acid (synthesized in reagent preparation 22, step 1) (500 mg, 2.6 mmol) methanol (25 mL) and concentrated sulfuric acid (1.25 mL) was stirred at 60° C. for 18 hours. The reaction mixture was cooled concentrated, diluted with ethyl acetate (50 mL), washed with water (50 mL), saturated aqueous sodium bicarbonate solution (2×30 mL), brine (30 mL), dried over sodium sulfate, filtered and concentrated to give the methyl 4-amino-2-methyl-3-nitrobenzoate (400 mg, 75% yield), MS (EI) for C9H10N2O4: 211 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated
  3. additiondiluted with ethyl acetate (50 mL)
  4. washwashed with water (50 mL), saturated aqueous sodium bicarbonate solution (2×30 mL), brine (30 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d86a77f9e36d4964a7618e2bc16259f8
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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