Nitric Acid → HCID 86721358, compound

HRID 869528

Reaction equation

HRID 869528 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5].C(OC(=O)CCC)(=O)CCC.[N+:28]([O-])([OH:30])=[O:29].[OH-].[Na+]>O>[CH3:1][O:2][CH2:3][C:4]([NH:6][C:7]1[C:16]([N+:28]([O-:30])=[O:29])=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10])=[O:5]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7798Butyric anhydrideHCID 14798Sodium HydroxideHCID 836497Methyl 2-(2-methoxyacetamido)benzoate

Product 1

HCID 86721358HCID 86721358, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

[step 1] Methyl 2-(2-methoxyacetamido)benzoate (U.S. Pat. No. 5,091,403; 3.0 g, 13.4 mmol) was suspended in butyric anhydride (12.7 mL, 134.0 mmol), fuming nitric acid (2.3 mL, 51.1 mmol) was added dropwise under ice-cooling, and the mixture was stirred at 0° C. for 40 min. Water was added to the mixture, 4 mol/L aqueous sodium hydroxide solution was added dropwise to neutralize the mixture, and the mixture was extracted 3 times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v) to give methyl 2-(2-methoxyacetamido)-3-nitrobenzoate (1.9 g, 51%).

Workup

  1. temperaturecooling
  2. additionwas added dropwise
  3. extractionthe mixture was extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-60/40 v/v)

Sources & evidence

ORD record
ord-9cd116c4c1274faea0b7e4769178f31d
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Linked notes

Loading…