Carbon Dioxide → 2-Chloroquinoline-3-carboxylic acid

HRID 4785

反応式

HRID 4785 の反応式
C(NC(C)C)(C)C.C([Li])CCC.CCCCCC.[Cl:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.[C:30](=[O:32])=[O:31]>O1CCCC1>[Cl:19][C:20]1[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1

参加物

7

反応物 5

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 8058HexaneHCID 119282-ChloroquinolineHCID 178418339Butyllithium

生成物 1

HCID 8471632-Chloroquinoline-3-carboxylic acid収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-65 °C

実験手順

To a solution of 21.3 ml (0.15 mole) of diisopropyl amine in 300 ml of dry tetrahydrofuran under a continuous nitrogen blanket, at -70° C., was added 61.6 ml of 2.7M n-butyllithium in hexane (0.165 mole) while maintaining the temperature at -60° to -70° C. Subsequent to this addition, the temperature was maintained at -65° C. for approximately 20 minutes. A solution of 20 g (0.12 mole) of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise while maintaining the temperature at -60° to -70° C. After holding the temperature at -65° C. for 20 minutes subsequent to this addition, the entire reaction mixture was poured onto a large excess of dry ice. Most of the solvent was evaporated in a stream of air; the residual solvent was removed by rotary evaporation. The residue was taken up in 300 ml water, made basic with dil aq. sodium hydroxide and washed with 3×50 ml of isopropyl ether. The aqueous layer was filtered and made acidic (4 to 5 pH) with dilute aqueous hydrochloric acid. The precipitate was collected, washed with water, isopropyl alcohol, and isopropyl ether, and dried, giving 15.4 g (62%) of white crystals, m.p. 190°-210° C. (decomp.). A sample was recrystallized from isopropyl alcohol giving an analytical sample, m.p. 190°-210° C. (decomp.).

後処理

  1. temperaturewhile maintaining the temperature at -60° to -70° C
  2. additionSubsequent to this addition
  3. temperaturewhile maintaining the temperature at -60° to -70° C
  4. customat -65° C.
  5. customfor 20 minutes
  6. additionsubsequent to this addition
  7. customthe entire reaction mixture
  8. customMost of the solvent was evaporated in a stream of air
  9. customthe residual solvent was removed by rotary evaporation
  10. washwashed with 3×50 ml of isopropyl ether
  11. filtrationThe aqueous layer was filtered
  12. customThe precipitate was collected
  13. washwashed with water, isopropyl alcohol, and isopropyl ether
  14. customdried

出典と根拠

ORDレコード
ord-b3282ab649924efeb49346007aa7bf75
出典データセット
uspto-grants-1988_02
特許番号
US04727152

関連ノート

読み込み中…