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Sodium Hydroxide → 6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid

HRID 331888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 331888
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][O:15][C:16]=2[CH3:17])=[N:6][CH:5]=1.[OH-].[Na+]>C(O)C>[CH3:17][C:16]1[O:15][N:14]=[C:13]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]=1[CH2:11][NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:24])=[O:2])=[CH:5][N:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 68443539Methyl 6-(((5-methyl-3-phenylisoxazol-4-yl)methyl)amino)nicotinate

Produkt 1

HCID 684464016-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-nicotinic acidAusbeute 91,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of 6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-nicotinic acid methyl ester (1.86 g, 5.50 mmol) in ethanol (100 mL) was added aqueous sodium hydroxide (1 N, 17 mL, 17 mmol) and the resulting suspension was heated to 80° C. for 0.5 h. After the solution was cooled to ambient temperature the solvent was distilled off and the residue was diluted with water (50 mL) and washed with tert-butylmethylether (50 mL). The organic layers were extracted with aqueous sodium hydroxide (1 N, 20 mL) and the combined aqueous layers were acified with aqueous hydrochloric acid (25%) to pH=3 and were extracted with a mixture of ethyl acetate and methanol (4:1, 30 mL). Drying over sodium sulfate and concentration afforded the title compound (1.55 g, 91%) which was obtained as a white solid. MS: m/e=310.3 [M+H]+.

Aufarbeitung

  1. temperatureAfter the solution was cooled to ambient temperature the solvent
  2. distillationwas distilled off
  3. additionthe residue was diluted with water (50 mL)
  4. washwashed with tert-butylmethylether (50 mL)
  5. extractionThe organic layers were extracted with aqueous sodium hydroxide (1 N, 20 mL)
  6. extractionwere extracted with a mixture of ethyl acetate and methanol (4:1, 30 mL)
  7. dry with materialDrying over sodium sulfate and concentration

Quellen und Nachweise

ORD-Eintrag
ord-c56de094703c49b5a67fd8233414cf49
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877782B2

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