Nitric Acid → HCID 21941232, compound

HRID 655213Notes

Reaction equation

HRID 655213 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.[N+:13]([O-:16])(O)=[O:14].[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:17](=[O:19])[CH3:18])=[C:7]([N+:13]([O-:16])=[O:14])[CH:6]=1

Participants

4

Reactant 3

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

Product 1

HCID 21941232HCID 21941232, compound

Procedure

A solution of 4-amino-phenyl acetic acid methyl ester (3 g, 18.2 mmol) in acetic anhydride (16 mL) was stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0° C. temperature and fuming nitric acid (2.3 mL) was added dropwise. The ice bath was removed and the reaction mixture was stirred for another 20 minutes before pouring it onto iced water. The resulting yellow precipitate was filtered, washed with water and dried in vacuo at 50° C. to give 3.7 g of the product. 1H NMR 500 MHz (DMSO) δ 2.05 (s, 3H), 3.63 (s, 3H), 3.81 (s, 2H), 7.54 (d, 1H), 7.58 (dd, 1H), 7.87 (d, 1H), 10.2 (s, 1H).

Workup

  1. additionwas added dropwise
  2. customThe ice bath was removed
  3. additionbefore pouring it onto iced water
  4. filtrationThe resulting yellow precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-5f55227ee9dd482890d4408692891cf0
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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