Benzylamine → HCID 22034129, compound

HRID 478326Notes

Reaction equation

HRID 478326 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:13]([NH:20][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[N+:10]([O-:12])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 114354124-CHLORO-6-METHYL-3-NITROPYRIDIN-2(1H)-ONE

Product 1

HCID 22034129HCID 22034129, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part A. A solution of 4-chloro-6-methyl-3-nitropyridone (5.0 g, 26.5 mmol) in acetonitrile (93 mL) was treated with benzylamine (2.89 mL, 26.5 mmol) and diisopropylethylamine (5.54 mL, 31.8 mmol). The mixture was heated to reflux for 4 hrs., then cooled to ambient temperature and allowed to stir for 12 hrs. The mixture was partitioned between dichloromethane and water (200 mL each), and the aqueous layer was extracted with dichloromethane (200 mL). The extracts were washed in sequence with water (200 mL) and combined, and the resulting precipitate was collected by filtration. The filtrate was dried over sodium sulfate, refiltered and evaporated to afford a second crop of crystalline product, 4-benzylamino-6-methyl-3-nitropyridone (6.74 g total, 26.0 mmol, 98%). m.p. 246-247° C. TLC RF 0.35 (10:90 isopropanol-ethyl acetate). 1H NMR (300 MHz, CDCl3): d 10.48 (1H, br s), 9.69 (1H, br s), 7.41-7.26 (5H, m), 5.66 (1H, s), 4.57 (2H, d, J=5.5 Hz), 2.26 (3H, s). MS (NH3—CI): m/e 261 (10), 260 (70), 226 (100).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hrs
  3. customThe mixture was partitioned between dichloromethane and water (200 mL each)
  4. extractionthe aqueous layer was extracted with dichloromethane (200 mL)
  5. washThe extracts were washed in sequence with water (200 mL)
  6. filtrationthe resulting precipitate was collected by filtration
  7. dry with materialThe filtrate was dried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-a621e08eff4846bd82a13399f8a67aa5
Source dataset
uspto-grants-2003_11
Patent number
US06642230B2

Reaction notes

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