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

HRID 567801

반응식

HRID 567801 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-89cd23090aa74a8ba08adfbb149b1cba
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06180627B2

연결된 노트

불러오는 중…