Nitric Acid → HCID 21941232, compound

HRID 2216244Notes

Reaction equation

HRID 2216244 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[C:13]([O:16]C(=O)C)(=O)[CH3:14].[N+:20]([O-])([OH:22])=[O:21]>O>[C:13]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][C:7]=1[N+:20]([O-:22])=[O:21])(=[O:16])[CH3:14]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 2761030Methyl 2-(4-aminophenyl)acetate

Product 1

HCID 21941232HCID 21941232, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 4-aminophenylacetate (110 g, 0.667 mol) was added dropwise to acetic anhydride (600 ml), maintaining the temperature of the reaction mixture below 30° C. by external cooling. Once the addition was complete the mixture was cooled to below 10° C. and concentrated nitric acid (85 ml) was added dropwise. Once the addition of the acid was complete, the mixture was allowed to warm to room temperature and poured onto a mixture of ice and water. The precipitated solid was collected by filtration and dried to give methyl 4-acetamido-3-nitrophenylacetate (120 g) as a pale yellow solid.

Workup

  1. temperaturemaintaining the temperature of the reaction mixture below 30° C. by external cooling
  2. additionOnce the addition
  3. temperaturewas cooled to below 10° C.
  4. additionOnce the addition of the acid
  5. filtrationThe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-37a29888ced942c2bac64a420b2d1a25
Source dataset
uspto-grants-2006_09
Patent number
US07112553B1

Reaction notes

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