Hydrochloric Acid → Imidazo-[1,2-a]quinoxaline-2-methanol

HRID 236321ノート

反応式

HRID 236321 の反応式
[CH:1]1[N:5]2[C:6]3[C:11]([N:12]=[CH:13][C:4]2=[N:3][C:2]=1[C:14](OCC)=[O:15])=[CH:10][CH:9]=[CH:8][CH:7]=3.[BH4-].[Li+].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:1]1[N:5]2[C:6]3[C:11]([N:12]=[CH:13][C:4]2=[N:3][C:2]=1[CH2:14][OH:15])=[CH:10][CH:9]=[CH:8][CH:7]=3

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 13228325Ethyl imidazo[1,2-a]quinoxaline-2-carboxylate

生成物 1

HCID 13770472Imidazo-[1,2-a]quinoxaline-2-methanol収率 82.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 7.2 g of ethyl imidazo-[1,2-a]-quinoxaline-2-carboxylate in 140 ml of anhydrous tetrahydrofuran and 1.0 g of lithium borohydride was refluxed with stirring for 20 hours and was then cooled to room temperature. 2N hydrochloric acid was added dropwise to the mixture until effervescence ceased and the clear solution was stirred for one hour and made alkaline with saturated sodium bicarbonate solution. The mixture was concentrated under reduced pressure to evaporate the tetrahydrofuran and the mixture was poured into 500 ml of water. The mixture was cooled in an ice bath and filtered to obtain 4.9 g of imidazo-[1,2-a]-quinoxaline-2-methanol in the form of a colorless solid. The filtrate was extracted with chloroform and the organic phase was dried over magnesium sulfate and evaporated to dryness to obtain an additional 0.60 g of the desired compound in the form of needles melting at 158°-159° C. after crystallization from an ether-ethyl acetate mixture.

後処理

  1. stirringthe clear solution was stirred for one hour
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto evaporate the tetrahydrofuran
  4. additionthe mixture was poured into 500 ml of water
  5. temperatureThe mixture was cooled in an ice bath
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-f79d77bdac604abd8e07d245de368092
出典データセット
uspto-grants-1987_02
特許番号
US04644002

反応ノート

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