4-Nitro-1H-indole → Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

HRID 551010

Reaktionsgleichung

Reaktionsgleichung von HRID 551010
P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([O-:12])=[O:11].[C:22]([O:26]N1CCCC1C)(=[O:25])[CH:23]=[O:24].[C:33]([O-])(O)=O.[Na+]>CO>[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:23](=[O:24])[C:22]([O:26][CH3:33])=[O:25])=[CH:16][NH:17]2)([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 1457664-Nitro-1H-indoleHCID 516892Sodium BicarbonateHCID 4432411Diphosphoryl tetrachlorideHCID 86629729HCID 86629729, Verbindung

Produkt 1

HCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Diphosphoryl chloride (0.938 mL, 6.80 mmol) was added dropwise to a solution of 4-nitroindole (1.00 g, 6.17 mmol) and methylpyrrolidinyl glyoxylate (Downie et al., Tetrahedron, 1993, 49, 4015-4034) (1.10 g, 6.80 mmol) at 0° C. and the mixture was allowed to warm to ambient temperature over 3 h. MeOH, then saturated aqueous NaHCO3 were added to the reaction at 0° C. and the solution was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo until crystals formed. The crystals were collected by vacuum filtration and two more crops were isolated from the filtrate to give the title compound. MS: m/z=249 (M+1).

Aufarbeitung

  1. extractionthe solution was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo until crystals
  5. customformed
  6. filtrationThe crystals were collected by vacuum filtration and two more crops
  7. customwere isolated from the filtrate

Quellen und Nachweise

ORD-Eintrag
ord-de507985d1204dcda4bf7f1491e21ea1
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947677B2

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