Methanol → HCID 58964475, compound

HRID 2069206Notes

Reaction equation

HRID 2069206 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]=1[NH:20]C(=O)C.CO.C(=O)(O)[O-].[K+]>C(OCC)(=O)C.O>[CH3:6][O:7][C:8](=[O:24])[C:9]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([N+:17]([O-:19])=[O:18])=[CH:11][C:10]=1[NH2:20]

Participants

7

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516893Potassium BicarbonateHCID 58964477HCID 58964477, compound

Product 1

HCID 58964475HCID 58964475, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.12 ml of sulfuric acid 98% are added dropwise at 0° C. (exothermic) to a suspension of 69 mg (0.257 mmol) of 2-acetylamino-5-methoxy-4-nitro-benzoic acid methyl ester, 0.69 ml of methanol and 0.12 ml of water. The mixture is then heated to 70° C. for 30 minutes, cooled to room temperature, poured onto a mixture of ice, water and ethyl acetate and the pH adjusted to 6 with concentrated potassium bicarbonate solution. The organic phase is separated, washed with brine, dried over sodium sulfate, filtered and evaporated, giving 46 mg (79%) of 2-amino-5-methoxy-4-nitro-benzoic acid methyl ester as red-brown crystals, m.p. 127-129° C.

Workup

  1. temperaturecooled to room temperature
  2. customThe organic phase is separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-078548694d594bfca9eb8158254a1b3b
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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