Sodium Hydroxide → 7-(3'-Dimethylaminophenyl)-6-methyl-1,6-naphthyridine-5(6H)-one

HRID 1065285Notes

Reaction equation

HRID 1065285 reaction equation
[CH3:1][NH:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[CH2:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH3:20])[CH3:19])[CH:13]=1.[OH-].[Na+]>C(O)C.O>[CH3:19][N:18]([CH3:20])[C:14]1[CH:13]=[C:12]([C:11]2[N:2]([CH3:1])[C:3](=[O:22])[C:4]3[CH:9]=[CH:8][CH:7]=[N:6][C:5]=3[CH:10]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 128333262-(3'-Dimethylaminobenzoylmethyl)nicotinic acid N-methylamide

Product 1

HCID 128333277-(3'-Dimethylaminophenyl)-6-methyl-1,6-naphthyridine-5(6H)-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The crude product of Example 7 (17.2 g.). was dissolved in ethanol and 4.3 g. of gaseous hydrogen chloride were bubbled in. The reaction mixture was heated for 5 minutes at 70° C. Two crops of a solid, 12.4 g., m.p. 197°-220° C. (dec.), and 1.9 g., m.p. 224°-226° (dec.), were obtained. The two crops were combined and recrystallized from ethanol to obtain 11.8 g., m.p. 221°-232° C. (dec.). The mother liquors from each of the crystallizations and recrystallizations were combined; two additional crops, 4.9 g. (total), m.p. 193°-216° C. (dec.), were obtained therefrom. 11.5 g. of the combined crystalline materials were dissolved in water, excess sodium hydroxide solution was added, and the basic solution was extracted with methylene chloride. The methylene chloride extract was dried over anhydrous sodium sulfate, filtered and evaporated at reduced pressure. The residue was chromatographed on silica gel using ethyl acetate as the eluant. The major fractions were combined and recrystallized from acetone/pentane, 7.6 g., m.p. 118°-120° C. An analytical sample had a melting point of 120° C. A second crop (2.4 g.), m.p. 117°-119° C., was also obtained.

Workup

  1. customof gaseous hydrogen chloride were bubbled in
  2. custom, m.p. 224°-226° (dec.), were obtained
  3. customrecrystallized from ethanol
  4. customto obtain 11.8 g
  5. customThe mother liquors from each of the crystallizations and recrystallizations
  6. custom(total), m.p. 193°-216° C. (dec.), were obtained
  7. extractionthe basic solution was extracted with methylene chloride
  8. extractionThe methylene chloride extract
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated at reduced pressure
  12. customThe residue was chromatographed on silica gel
  13. customrecrystallized from acetone/pentane, 7.6 g
  14. customA second crop (2.4 g.), m.p. 117°-119° C., was also obtained

Sources & evidence

ORD record
ord-2e7abca631ec4ee38da401d9be0b1d29
Source dataset
uspto-grants-1982_05
Patent number
US04329349

Reaction notes

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