Indole-5-carbonitrile → (1H-indol-5-yl)methanamine

HRID 567801

反応式

HRID 567801 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]#[N:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O-])(O)=O.[Na+]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][NH2:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 27513Indole-5-carbonitrileHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydride

生成物 1

HCID 54791(1H-indol-5-yl)methanamine収率 314%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A stirred solution of 1H-indole-5-carbonitrile (4.0 g, 28.1 mmol) in THF (50 ml) at 0° C. was treated dropwise with lithium aluminum hydride in THF (1M, 98 ml, 98 mmol). The resultant mixture was stirred, warming to room temperature overnight. Sat. aq. NaHCO3 (60 ml) was added at 0° C. and resultant mixture was filtered through filter agent celite 521 and washed with THF. Evaporation of the solvent gave the crude product which was purified by chromatography (SiO2, gradient elution with 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3) to give the desired product (white powder, 12.9 g, 71%). 1H NMR (CD3OD) δ 4.10 (s, 2H), 6.50 (d, 1H), 7.15 (d, 1H), 7.30 (d, 1H), 7.40 (d, 1H), 7.60 (s, 1H). LRMS m/z=147.2 (M+1)+.

後処理

  1. filtrationresultant mixture was filtered
  2. filtrationthrough filter agent celite 521
  3. washwashed with THF
  4. customEvaporation of the solvent
  5. customgave the crude product which
  6. customwas purified by chromatography (SiO2, gradient elution with 95:5 CH2Cl2:MeOH; 90:10 CH2Cl2:MeOH; 90:10:1 CH2Cl2:MeOH:NH3)

出典と根拠

ORDレコード
ord-89cd23090aa74a8ba08adfbb149b1cba
出典データセット
uspto-grants-2001_01
特許番号
US06180627B2

関連ノート

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