Tetrahydrofuran → 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine

HRID 1862216

反応式

HRID 1862216 の反応式
[CH2:1]([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1=[N:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1>CCCCCC>[CH2:1]([N:8]1[C:9]2=[N:13][C:14]3[C:15]([C:16]([NH2:17])=[C:10]2[CH2:11][CH2:12]1)=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 8028TetrahydrofuranHCID 7584062-(1-Benzyl-pyrrolidin-2-ylideneamino)benzonitrile

生成物 1

HCID 7119891-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine収率 39%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-10 °C

実験手順

The compound 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine (Compound 25) was synthesized by first cooling a solution of Compound 24 (37.6 g, 0.14 mol) and tetrahydrofuran (350 mL) to −35° C. under argon atmosphere and adding a solution of hexane (110 mL) and lithium diisopropylamine-tetrahydrofuran complex (0.35 mol) dropwise. The temperature of the mixture was then gradually raised to −10° C. and ice-water (30 mL) was added dropwise. Organic solvent was evaporated under reduced pressure and the mixture was extracted with chloroform. The combined organic extracts were dried with anhydrous sodium sulfate and condensed under vacuum. The residue was treated with ethanol (15 mL) and crystals precipitated. The precipitate was filtered, washed with cold ethanol and dried under vacuum to yield 14.6 g (39%) of Compound 25 as needles; mp 174-176° C.; IR (KBr): 3411, 3116, 1654, 1502, 1350, 756 cm−1; 1H NMR (DMSO-d6): δ 7.01-7.93 (m, 9H), 6.05 (s, 2H), 4.60 (s, 2H), 3.37 (t, 2H), 2.87 (t, 2H); 13C NMR (CDCl3): δ 162.7, 149.3, 144.8, 138.8, 128.7, 128.2, 128.1, 127.2, 126.2, 121.8, 119.9, 117.6, 100.7, 48.4, 23.3. Anal. Calcd. for C18H17N3(275.35): C, 78.52; H, 6.22; N, 15.26. Found: C, 78.07; H, 6.07; N, 15.08.

後処理

  1. customThe compound 1-Benzyl-2,3-dihydro-1H-pyrrolo[2,3-b]quinolin-4-ylamine (Compound 25) was synthesized
  2. customOrganic solvent was evaporated under reduced pressure
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe combined organic extracts were dried with anhydrous sodium sulfate and condensed under vacuum
  5. additionThe residue was treated with ethanol (15 mL) and crystals
  6. customprecipitated
  7. filtrationThe precipitate was filtered
  8. washwashed with cold ethanol
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-d1738b02e37a481d83ef11f1bbf8b318
出典データセット
uspto-grants-2003_03
特許番号
US06537993B2

関連ノート

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