Methane → alpha-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

HRID 274367ノート

反応式

HRID 274367 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17](O)(=O)[CH:18]([CH3:20])[OH:19].C>Cl>[CH3:17][CH:18]([C:20]1[N:12]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=1)[OH:19]

参加物

5

反応物 3

HCID 297MethaneHCID 612Lactic AcidHCID 11298872N4-(2-methylpropyl)quinoline-3,4-diamine

生成物 1

HCID 15224403alpha-Methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-methanol

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

反応条件

温度
140 °C

実験手順

3-Amino-4-(2-methylpropylamino) quinoline (29.0 g; 0.135 mol) and lactic acid (36 mL; 0.48 mol) were mixed and heated at 140° C. for 6 hr. The mixture was then dissolved in dilute hydrochloric acid and treated with charcoal. The solids were filtered from the mixture. The filtrate was made basic with ammonium hydroxide to precipitate the product as an oil. The oil was extracted into ethyl acetate. The ethyl acetate solution was treated with decolorizing carbon and the solids were filtered from the mixture. The filtrate was evaporated to dryness to yield a greenish oil which was pure enough for further reactions. A small sample was triturated with hexane to obtain a solid which was recrystallized from ethyl acetate for analysis. m.p. 152°-166° C.

後処理

  1. filtrationThe solids were filtered from the mixture
  2. customto precipitate the product as an oil
  3. extractionThe oil was extracted into ethyl acetate
  4. additionThe ethyl acetate solution was treated with decolorizing carbon
  5. filtrationthe solids were filtered from the mixture
  6. customThe filtrate was evaporated to dryness
  7. customto yield a greenish oil which
  8. customA small sample was triturated with hexane
  9. customto obtain a solid which
  10. customwas recrystallized from ethyl acetate for analysis

出典と根拠

ORDレコード
ord-af473ad86e2c45b78250bba5149418dd
出典データセット
uspto-grants-1995_02
特許番号
US05389640

反応ノート

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