Succinic anhydride → 4-[[4-[(2-Methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acid

HRID 1603242Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603242
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>ClCCl.N1C=CC=CC=1.CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:12][CH:13]=1

Komponenten

6

Edukt 2

HCID 7922Succinic anhydrideHCID 131356894-[(2-Methoxyethoxy)methoxy]aniline

Produkt 1

HCID 196090764-[[4-[(2-Methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acidAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 510 mg (2.58 mmol) of 4-[(2-methoxyethoxy) methoxy]benzenamine (22) in 8 mL of dichloromethane and 2 mL of anhydrous pyridine (Aldrich) was added 380 mg (3.8 mmol) of succinic anhydride portionwise. The mixture was stirred at room temperature for 18 hours. To the reaction mixture was added 20 mL of methanol and the mixture was stirred at room temperature for 2 hours. The mixture was concentrated and purified by preparative thin layer chromatography using 8:2 chloroform:methanol as an eluent to yield 420 mg (1.41 mmol, 55%) of 4-[[4-[(2-methoxyethoxy)methoxy]phenyl]amino]-4-oxobutanoic acid (23). NMR, IR and MS data confirmed the compound identity.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. concentrationThe mixture was concentrated
  3. custompurified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e37b7dd84098450aaf28a32dee369281
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986094

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