1-Nitropropane → 7-bromo-5-chloro-1H-indole-3-carbonitrile

HRID 913965

Reaktionsgleichung

Reaktionsgleichung von HRID 913965
[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]=O.P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+].[N+:22](CCC)([O-])=O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]#[N:22]

Komponenten

5

Edukt 3

HCID 79031-NitropropaneHCID 159282Ammonium phosphate, tribasicHCID 575461137-bromo-5-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 575462207-bromo-5-chloro-1H-indole-3-carbonitrileAusbeute 54,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 7-bromo-5-chloro-1H-indole-3-carbaldehyde (0.80 g, 3.09 mmol), Ammonium phosphate, dibasic (1.269 mL, 15.47 mmol), and 1-nitropropane (0.276 mL, 3.09 mmol) in Acetic Acid (20 mL) was heated at reflux. The solvent was evaporated, the residue was taken up in aqueous sodium bicarbonate (300 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were dried with MgSO4 and evaporated. The residue was purified by chromatography on SiO2 with 20%-25% ethyl acetate/hexanes to give 7-bromo-5-chloro-1H-indole-3-carbonitrile (0.43 g, 1.683 mmol, 54.4% yield) as a yellow solid. 1H-NMR (CDCl3, 400 MHz) δ 8.27 (bs, 1H), 7.79 (s, 1H), 7.72 (d, J=1.8 Hz, 1H), 7.49 (d, J=1.8 Hz, 1H). LC/MS (HPLC method 4): tR=3.12 min, 255.01(MH)+.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe organic layers were dried with MgSO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 with 20%-25% ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b014e68c04824017b8e7a4fd2023d96d
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026257B2

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