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

HRID 1065285ノート

反応式

HRID 1065285 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2e7abca631ec4ee38da401d9be0b1d29
出典データセット
uspto-grants-1982_05
特許番号
US04329349

反応ノート

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