p-Nitroacetophenone → HCID 88069650, compound

HRID 991557Notes

Reaction equation

HRID 991557 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][CH2:11][C:12]([OH:14])=[O:13])=O)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1)=O.C([O-])(=O)C.[Pb+4].C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.C(OC(=O)C)(=O)C>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[O:14][C:12](=[O:13])/[C:11](=[C:16](/[C:18]3[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=3)\[CH3:15])/[N:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 7487p-NitroacetophenoneHCID 7918Acetic AnhydrideHCID 53558Glycine, N-(2-chloronicotinoyl)-HCID 178418268HCID 178418268, compound

Product 1

HCID 88069650HCID 88069650, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-{[(2-chloro-3-pyridinyl)carbonyl]amino}acetic acid (6.44 g, 30 mmol, prepared from glycine and 2-chloronicotinoyl chloride), 4-nitroacetophenone (2.48 g, 15 mmol), lead (IV) acetate (3.33 g, 7.5 mmol) and acetic anhydride in THF (30 ml) was heated at reflux for 4 days. The mixture was poured onto crushed ice, the solid filtered off, washed with water and dried. The brown solid was triturated twice with boiling ethanol and filtered off to give the title compound as a brown solid (1.07 g). δH (CDCl3), 8.57 (1H, dd, J 4.8, 2.1 Hz, PyH), 8.34-8,29 (3H, m, ArH+PyH), 8.05 (2H, d, J 9.1 Hz, ArH), 7.41 (1H, dd, J 7.9, 4.8 Hz, PyH) and 2.84 (3H, s, Me).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. additionThe mixture was poured
  4. customonto crushed ice
  5. filtrationthe solid filtered off
  6. washwashed with water
  7. customdried
  8. customThe brown solid was triturated twice with boiling ethanol
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-4f34db70fe8f424a802c52c2d1c949a8
Source dataset
uspto-grants-2002_10
Patent number
US06465471B1

Reaction notes

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