Isatoic Anhydride → 2-amino-N-(2-hydroxyethoxy)benzamide

HRID 1045982

Reaktionsgleichung

Reaktionsgleichung von HRID 1045982
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])OC1=O.S([O:17][CH2:18][CH2:19][O:20][NH2:21])(O)(=O)=O>>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:21][O:20][CH2:19][CH2:18][OH:17])=[O:11]

Komponenten

3

Edukt 2

HCID 8359Isatoic AnhydrideHCID 1317309242-(Aminooxy)ethanol hemisulfate

Produkt 1

HCID 866551452-amino-N-(2-hydroxyethoxy)benzamideAusbeute 66,6 %

Versuchsvorschrift

1H-3,1-benzoxazine-2,4-dione (320 mg, 1.96 mmol) and 2-(aminooxy)ethanol hemisulfate (990 mg, 3.92 mmol) were reacting using the procedure of example 15.07, starting material. The crude product was purified by flash chromatography on silica gel eluting with 0 to 80% EtOAc in DCM. The solvent was evaporated to dryness to afford 2-amino-N-(2-hydroxyethoxy)benzamide (256 mg, 66.5%) as a pale yellow oil which solidified on standing. NMR Spectrum: (DMSOd6) 3.57-3.64 (m, 2H), 3.85-3.92 (m, 2H), 4.75 (bs, 1H), 6.27 (bs, 2H), 6.49 (dd, 1H), 6.71 (d, 1H), 7.15 (ddd, 1H), 7.34 (dd, 1H), 11.39 (bs, 1H); Mass spectrum: MH+ 197

Aufarbeitung

  1. customThe crude product was purified by flash chromatography on silica gel eluting with 0 to 80% EtOAc in DCM
  2. customThe solvent was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8d9b298418e94afd8b991bd758e653d0
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569298B2

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