Aluminum(III) Chloride → 1-Methyl-1H-indazol-5-ol

HRID 909163ノート

反応式

HRID 909163 の反応式
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[N:7]=[CH:6]2.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[CH3:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[CH:6]=[N:7]1

参加物

4

反応物 2

HCID 6451240Aluminum(III) ChlorideHCID 574187495-Methoxy-1-methylindazole

生成物 1

HCID 441192401-Methyl-1H-indazol-5-ol収率 13.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of (2t) (0.99 g, 6.1 mmol) in toluene (30 mL) was added AlCl3 (2.44 g, 18.3 mmol) at room temperature, upon which a purple colored mixture formed. After refluxing for 20 minutes, an olive colored mixture formed. The mixture was refluxed for 2 hours, allowed to cool to room temperature and poured into an ice-water bath. The insoluble solids were collected by filtration (398 mg). The filtrate was extracted with DCM, filtered through IPS paper, evaporated in vacuo and purified on the Biotage eluting with (1:9) then (3:7) Et2O/DCM and finally (1:1) DCM/Et2O. The product fractions were evaporated in vacuo affording compound (3t) as a brown foam (122 mg). Total combined yield, 520 mg (58%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 149 (M+H) detected.

後処理

  1. customupon which a purple colored mixture formed
  2. temperatureAfter refluxing for 20 minutes
  3. customan olive colored mixture formed
  4. temperatureThe mixture was refluxed for 2 hours
  5. additionpoured into an ice-water bath
  6. filtrationThe insoluble solids were collected by filtration (398 mg)
  7. extractionThe filtrate was extracted with DCM
  8. filtrationfiltered through IPS paper
  9. customevaporated in vacuo
  10. custompurified on the Biotage
  11. washeluting with (1:9)
  12. customThe product fractions were evaporated in vacuo

出典と根拠

ORDレコード
ord-e404189fbd3f4489b3d6867a2e7842a0
出典データセット
uspto-grants-2011_09
特許番号
US08017641B2

反応ノート

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