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Water → (1-Biphenyl-2-ylmethyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid hydrazide

HRID 2292793
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2292793
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH2:22])=[O:21])=[C:9]1[CH3:23].C(OC(=O)CC1C2C(=CC=C(OC)C=2)[N:37](CC2C=CC=CC=2C2C=CC=CC=2)C=1C)C.NN.O>C(O)C>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:20]([NH:22][NH2:37])=[O:21])=[C:9]1[CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 9321HydrazineHCID 10500247HCID 10500247, VerbindungHCID 107642291-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester

Produkt 1

HCID 10834763(1-Biphenyl-2-ylmethyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetic acid hydrazide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

1-([1,1'-Biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetamide. A mixture of 1.18 g (2.86 mmol) of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester and 3 mL of hydrazine in 20 mL of ethanol was heated to maintain reflux for 16 hours. After cooling, water was added and the mixture was extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4), and concentrated to give 1.02 g of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid hydrazide. A mixture of 576 mg (1.44 mmol) of this material and 300 mg of Raney Ni in 20 mL of ethanol was heated to maintain reflux for 3 hours. After cooling the solvent was decanted and the Raney Ni washed twice with methylene chloride. The combined organic solvents were concentrated at reduced pressure and the residue chromatographed on silica gel and eluted with ethyl acetate to give 369 mg (67% yield) of 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetamide.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 16 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-abc00abda5db4878873adf7bba1660ff
Quelldatensatz
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05684034

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