Indole-3-Butyric Acid → 4-[1-(3-Nitrobenzyl)indol-3-yl]butyric acid

HRID 1974563

Reaktionsgleichung

Reaktionsgleichung von HRID 1974563
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4]1.[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br)([O-:20])=[O:19]>CN(C)C=O>[N+:18]([C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4]1)([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 8617Indole-3-Butyric AcidHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-

Produkt 1

HCID 191017574-[1-(3-Nitrobenzyl)indol-3-yl]butyric acidAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a suspension of sodium hydride (60% dispersion in mineral oil) (0.59 g) in N,N-dimethylformamide (10 ml) was added a solution of 4-(3-indolyl)butyric acid (1.0 g) in N,N-dimethylformamide (5 ml). The mixture was stirred at room temperature for 30 minutes and cooled at -40° C. To the mixture was added a solution of 3-nitrobenzyl bromide (1.06 g) in N,N-dimethylformamide (5 ml). The mixture was stirred at -40° C. for 20 minutes and partitioned between ethyl acetate and 7% hydrochloric acid. The organic layer was washed with water, dried over magnesium sulfate and evaporated. The residue was washed with diisopropyl ether to give 4-[1-(3-nitrobenzyl)indol-3-yl]butyric acid as a white powder (1.20 g).

Aufarbeitung

  1. temperaturecooled at -40° C
  2. stirringThe mixture was stirred at -40° C. for 20 minutes
  3. custompartitioned between ethyl acetate and 7% hydrochloric acid
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. washThe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-02bfec7440644823a74f27c76fe0cd28
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283251

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