Pyridine → HCID 13607936, compound

HRID 1981595Notes

Reaction equation

HRID 1981595 reaction equation
[C:1]([C:4]1[CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[C:6]([C:12]([OH:14])=[O:13])=[C:7]([CH3:11])[NH:8][C:9]=1[CH3:10])(=O)[CH3:2].Cl.[NH2:25][OH:26].N1[CH:32]=[CH:31]C=CC=1>C(O)C>[CH2:31]([O:14][C:12]([C:6]1[CH:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-:23])=[O:22])[CH:4]2[C:1]([CH3:2])=[N:25][O:26][C:9]2([CH3:10])[NH:8][C:7]=1[CH3:11])=[O:13])[CH3:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 20082998HCID 20082998, compound

Product 1

HCID 13607936HCID 13607936, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-acetyl-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3-pyridinecarboxylic acid (J. A. Berson and E. Brown, J. Amer. Chem. Soc., 77, 444 (1955), 2.34 g), hydroxylamine hydrochloride (0.71 g), pyridine (0.81 g), and ethanol (50 mL)) was heated under reflux on a steam bath for 4 hours, then evaporated on a rotary evaporator. The residue was dissolved in hot methanol, and the solution was filtered. The filtrate was concentrated on a rotary evaporator, and chilled in an ice-bath to cause a separation of a precipitate. The precipitate was collected on a filter, and recrystallized once more from methanol to give the titled product (0.1 g), mp 211.5°-212.5° C.

Workup

  1. temperatureunder reflux on a steam bath for 4 hours
  2. customevaporated on a rotary evaporator
  3. dissolutionThe residue was dissolved in hot methanol
  4. filtrationthe solution was filtered
  5. concentrationThe filtrate was concentrated on a rotary evaporator
  6. temperaturechilled in an ice-bath
  7. customa separation of a precipitate
  8. customThe precipitate was collected on a filter
  9. customrecrystallized once more from methanol

Sources & evidence

ORD record
ord-bc85887e34de4bed907f53e6900a0b9e
Source dataset
uspto-grants-1986_06
Patent number
US04593100

Reaction notes

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