Phosphorus oxychloride → HCID 22034114, compound

HRID 1856679Notes

Reaction equation

HRID 1856679 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[NH:12][C:11](=O)[C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:22])=O.C([O-])(O)=O.[Na+]>ClCCl>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([Cl:22])[C:10]=1[N+:17]([O-:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 22034129HCID 22034129, compound

Product 1

HCID 22034114HCID 22034114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Part B. A solution of the pyridone from Part A (6.72 g, 25.9 mmol) in phosphorus oxychloride (52 mL, 25.5 mmol) was stirred at ambient temperature for 3 d. The reaction mixture was poured into a mixture of ice (150 g) and dichloromethane (200 mL). After the ice had melted, 100 mL more dichloromethane was added, and the pH of the mixture was adjusted to 7 with solid NaHCO3. The mixture was separated, and the aqueous phase was extracted with dichloromethane. The extracts were combined, dried over sodium sulfate, filtered and evaporated to afford the product (4-benzylamino-2-chloro-6-methyl-3-nitropyridine) as a bright yellow crystalline solid (6.45 g, 23.2 mmol, 90%). TLC RF 0.76 (ethyl acetate). 1H NMR (300 MHz, CDCl3): d 7.43-7.26 (5H, m), 7.04 (1H, br), 6.47 (1H, s), 4.48 (2H, d, J=5.5 Hz), 2.40 (3H, s). MS(NH3 -CI): m/e 281 (5), 280 (35), 279 (17), 278 (100).

Workup

  1. customThe mixture was separated
  2. extractionthe aqueous phase was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-50ee9b7a803a480695fc77715285b9ca
Source dataset
uspto-grants-2000_11
Patent number
US06143743

Reaction notes

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