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Sodium Bicarbonate → HCID 178433793, Verbindung

HRID 238712
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238712
Br.[NH2:2][C:3]1[C:4]([OH:17])=[C:5]([C:9]2[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:18]([O-])=O.[Na+].[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([N:31]3[C:35](=[O:36])[CH2:34][C:33]([CH3:37])=[N:32]3)=[CH:28][CH:29]=2)[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>Cl.C(O)C>[OH:17][C:4]1[C:3]([NH:2]/[N:18]=[C:34]2/[C:33]([CH3:37])=[N:32][N:31]([C:27]3[CH:26]=[C:25]4[C:30](=[CH:29][CH:28]=3)[CH2:22][CH2:23][CH2:24]4)[C:35]/2=[O:36])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[O:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574838055-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide

Produkt 1

HCID 178433793HCID 178433793, VerbindungAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

5-(3-Amino-2-hydroxy-phenyl)-furan-2-carboxylic acid hydrobromide 4g (300 mg, 1.0 mmol) was dissolved in hydrochloric acid (3.4 mL, 1 M) followed by dropwise addition of 1.2 mL of sodium nitrite solution (73 mg, 1.05 mmol) upon cooling by an ice-water bath. After the mixture was reacted for 10 minutes, 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (193 mg, 0.9 mmol), sodium bicarbonate (1.26 g, 15 mmol) and 4.4 mL of ethanol were added successively. The mixture was reacted at room temperature for 24 hours. The mixture was filtered and the filter cake was washed with 20 mL of water and then dissolved in 20 mL of water. Upon cooling by an ice-water bath, the mixture was adjusted to pH<5 with concentrated hydrochloric acid, filtered and dried to obtain the title compound (Z)-5-{2-hydroxy-3-[N′-(1-indan-5-yl-3-methyl-5-oxo-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-phenyl}-furan-2-carboxylic acid 16a (287 mg, yield 71.8%) as a yellow solid.

Aufarbeitung

  1. temperatureupon cooling by an ice-water bath
  2. customAfter the mixture was reacted for 10 minutes
  3. customThe mixture was reacted at room temperature for 24 hours
  4. filtrationThe mixture was filtered
  5. washthe filter cake was washed with 20 mL of water
  6. dissolutiondissolved in 20 mL of water
  7. temperatureUpon cooling by an ice-water bath
  8. filtrationfiltered
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-49180287b8804a7b8ccd5c139b4b1562
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642637B2

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