Nitric Acid → Methyl 4-acetamido-2-methoxy-5-nitrobenzoate

HRID 1465804Notes

Reaction equation

HRID 1465804 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C>[C:1]([NH:4][C:5]1[C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:15][CH3:16])[CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 77720Methyl 4-(acetylamino)-2-methoxybenzoate

Product 1

HCID 77723Methyl 4-acetamido-2-methoxy-5-nitrobenzoateYield 84%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
0 °C

Procedure

To methyl 4-acetamido-2-methoxybenzoate (299 mg, 1.34 mmol) in acetic anhydride (3 ml) stirred under nitrogen at −10° C. was added concentrated nitric acid (0.35 ml) dropwise. After then stirring at 0° C. for 10 min the reaction mixture was partitioned between ethyl acetate (20 ml) and water (20 ml). The aqueous layer was further extracted with ethyl acetate (2×10 ml) and the combined organic extract washed with saturated sodium bicarbonate solution (2×10 ml), brine (2×10 ml), dried (MgSO4) and evaporated to give methyl 4-acetamido-2-methoxy-5-nitrobenzoate (301 mg, 84%) as a dull orange powder.

Workup

  1. customwas partitioned between ethyl acetate (20 ml) and water (20 ml)
  2. extractionThe aqueous layer was further extracted with ethyl acetate (2×10 ml)
  3. extractionthe combined organic extract
  4. washwashed with saturated sodium bicarbonate solution (2×10 ml), brine (2×10 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-266fad43a3674fb4ae2f38ca5a76009a
Source dataset
uspto-grants-2015_04
Patent number
US08999993B2

Reaction notes

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