Hydrazine hydrate (1:1) → 4-(1,3-Dihydro-2-benzofuran-5-yloxy)aniline

HRID 716824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 716824
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:19]=[CH:18][C:14]3[CH2:15][O:16][CH2:17][C:13]=3[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>C(O)C.[Pd]>[CH2:15]1[C:14]2[CH:18]=[CH:19][C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)=[CH:12][C:13]=2[CH2:17][O:16]1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 710901375-[(4-Nitrophenyl)oxy]-1,3-dihydro-2-benzofuran2×

Produkt 1

HCID 867157014-(1,3-Dihydro-2-benzofuran-5-yloxy)anilineAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 5-[(4-nitrophenyl)oxy]-1,3-dihydro-2-benzofuran (Intermediate 74, 190 mg, 0.739 mmol), hydrazine hydrate (0.046 ml, 1.477 mmol) and Pd/C (157 mg, 0.148 mmol) in ethanol (6 ml) was stirred under argon at 90° C. After 4.5 hours 0.2 equivalents of Pd/C and 2 equivalents of hydrazine hydrate were added. After 1 more hour, the reaction mixture was cooled to room temperature and then filtered over celite and washed with methanol. The organic phase was concentrated and the residue was purified by SCX to afford the title compound (152 mg).

Aufarbeitung

  1. filtrationfiltered over celite
  2. washwashed with methanol
  3. concentrationThe organic phase was concentrated
  4. customthe residue was purified by SCX

Quellen und Nachweise

ORD-Eintrag
ord-69df83a1bb95442f9472e7a3ade9155f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193704B2

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