Water → HCID 798732, compound

HRID 727093Notes

Reaction equation

HRID 727093 reaction equation
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C[C:14]1[CH:22]=[N:21][CH:20]=[CH:19][C:15]=1[C:16](N)=O.O>O1CCCC1.ClCCl>[C:2]1([C:1]2[N:8]=[C:16]([C:15]3[CH:14]=[CH:22][N:21]=[CH:20][CH:19]=3)[O:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 69186N'-HydroxybenzenecarboximidamideHCID 27624893-methylpyridine-4-carboxamide

Product 1

HCID 798732HCID 798732, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a mixture of benzamide oxime (12.8 g, 94 mmol) and 4 Å sieves (80 g) in tetrahydrofuran (250 ml) under a nitrogen atmosphere was carefully added sodium hydride (55% dispersed in oil, 4.3 g, 98 mmol) portionwise. When addition was complete the reaction was heated at 50° C. for 1 hour. Methyl isonicotinamide (5.6 ml, 47 mmol) in tetrahydrofuran (50 ml) was added, and the reaction stirred at reflux for 2 hours. The reaction was cooled to room temperature and water (200 ml) and dichloromethane (300 ml) added. The mixture was filtered through a pad of Celite and the two phases separated. The aqueous phase was extracted with a further portion of dichloromethane (250 ml). The combined organic phases were washed with saturated brine (200 ml), dried (MgSO4) and evaporated in vacuo. The residue was triturated with ethyl acetate to yield the title compound as a white solid (2.64 g, 25%). δH (CDCl3) 7.50-7.56 (3H, m, ArH), 8.05-8.07 (2H, m, ArH), 8.16-8.19 (2H, m, ArH), 8.89 (2H, dd, J 4.4, 1.6 Hz, pyridyl 2-H, 6-H).

Workup

  1. additionWhen addition
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationThe mixture was filtered through a pad of Celite
  5. customthe two phases separated
  6. extractionThe aqueous phase was extracted with a further portion of dichloromethane (250 ml)
  7. washThe combined organic phases were washed with saturated brine (200 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-ca57ee9035b54a87aeaaf53d0d0c571f
Source dataset
uspto-grants-1998_01
Patent number
US05712285

Reaction notes

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