Benzaldehyde → 3-(Hydroxyphenylmethyl)indole-5-carbonitrile

HRID 1247496

Reaktionsgleichung

Reaktionsgleichung von HRID 1247496
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)#[N:2].[CH:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CO>[OH:19][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=2)[NH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 27513Indole-5-carbonitrile

Produkt 1

HCID 219076233-(Hydroxyphenylmethyl)indole-5-carbonitrileAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 5-cyanoindole (2.84 g, 20 mmol) and benzaldehyde (4.24 g, 40 mmol) in MeOH (100 mL) was treated with powdered NaOH (0.8 g, 20 mmol) and stirred at rt for 4 days. The solvent was partially removed in vacuo and the residue diluted with CH2Cl2, washed with water (3×), and dried over Na2SO4, filtered and evaporated to a solid which was triturated with hexanes to provide 3-(hydroxyphenylmethyl)indole-5-carbonitrile as a light yellow solid (4.9 g, 98%).

Aufarbeitung

  1. customThe solvent was partially removed in vacuo
  2. additionthe residue diluted with CH2Cl2
  3. washwashed with water (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to a solid which
  7. customwas triturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-84e14c59e439402a9c14162b2e3ae2f0
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129264B2

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