Nitric Acid → HCID 19045250, compound

HRID 1591227Notes

Reaction equation

HRID 1591227 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[CH:6][C:5]=1[OH:14])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C.[N+:22]([O-])([OH:24])=[O:23].O>ClCCl>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([N+:22]([O-:24])=[O:23])[C:5]=1[OH:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 2775185N-(4-acetyl-3-hydroxyphenyl)acetamide

Product 1

HCID 19045250HCID 19045250, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of N-(4-acetyl-3-hydroxyphenyl)acetamide (9.66 g, 50 mmol) and acetic anhydride (14.2 ml, 15.3 g, 150 mmol) in dichloromethane (150 ml) was cooled to 5° C. and nitric acid (90%, d 1.49, 4.70 ml, 7.00 g, 100 mmol) was added dropwise. The mixture was stirred at room temperature for 1 hour, poured into water (150 ml) and extracted with dichloromethane (3×150 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure and the residue was purified by repeated flash column chromatography on silica gel, eluting with hexane/30% ethyl acetate then hexane/50% ethyl acetate. The first isomer to elute was N-(4-acetyl-5-hydroxy-2-nitrophenyl)acetamide as a yellow solid (3.87 g, 33%).

Workup

  1. extractionextracted with dichloromethane (3×150 ml)
  2. dry with materialThe combined organic fractions were dried (Na2SO4)
  3. customevaporated under reduced pressure
  4. customthe residue was purified by repeated flash column chromatography on silica gel
  5. washeluting with hexane/30% ethyl acetate
  6. washThe first isomer to elute

Sources & evidence

ORD record
ord-f25ae0486a3f481ca7ed1d46b5914bdd
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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