Nitric Acid → HCID 86657417, compound

HRID 1481561Notes

Reaction equation

HRID 1481561 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:14][C:13](=[O:15])[CH:12]=[C:11]([OH:16])[CH:10]=1.[N+:17]([O-])([OH:19])=[O:18]>CC(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:14][C:13](=[O:15])[C:12]([N+:17]([O-:19])=[O:18])=[C:11]([OH:16])[CH:10]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 67412521HCID 67412521, compound

Product 1

HCID 86657417HCID 86657417, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

6-(2,6-Dichlorophenyl)-4-hydroxy-1H-pyridin-2-one (253 mg, 0.990 mmol, prepared as described in the previous step) was placed in a 8 mL vial equipped with a stir bar and AcOH (4 mL) was added. Concentrated HNO3 (0.540 mL, 12.0 mmol) was added via syringe and the vial was capped and stirred at 60° C. for 14 hr. The resulting mixture was cooled to room temperature and poured onto crushed ice (20 mL). The precipitate was isolated by filtration and washed with H2O (10 mL). The solid was air-dried to yield 6-(2,6-Dichloro-phenyl)-4-hydroxy-3-nitro-1H-pyridin-2-one as a yellow powder. The filtrate was extracted with EtOAc (3×10 mL) and the combined extracts were washed with H2O (20 mL), dried over MgSO4 and filtered. The solvent was removed under reduced pressure to yield an additional crop of 6-(2,6-dichloro-phenyl)-4-hydroxy-3-nitro-1H-pyridin-2-one. 1H-NMR (400 MHz, CD3OD) δ: 7.48-7.61 (m, 3H), 6.13 (s, 1H).

Workup

  1. customvial equipped with a stir bar
  2. customthe vial was capped
  3. temperatureThe resulting mixture was cooled to room temperature
  4. additionpoured
  5. customThe precipitate was isolated by filtration
  6. washwashed with H2O (10 mL)
  7. customThe solid was air-dried

Sources & evidence

ORD record
ord-379497022f1945c7b7a516de35eecf49
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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