Methylamine → 4-Chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarate

HRID 1178476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178476
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]=O)[C:12]=2[O:19][CH2:20][CH3:21])[CH:3]=1.CN.[C:24]([BH3-])#[N:25].[Na+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][NH:25][CH3:24])[C:12]=2[O:19][CH2:20][CH3:21])[CH:3]=1

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303824-Chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrile

Produkt 1

HCID 219303734-Chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarateAusbeute 67,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

4-Chloro-2-(2-ethoxy-3-formylphenoxy)benzonitrile (0.55 g, 1.8 mmol), methylamine (2M in methanol, 3.0 mL, 6.0 mmol) and sodium cyanoborohydride (0.13 g, 2.1 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (55 mL) for 3 days. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. Fumaric acid (0.21 g, 1.8 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated overnight with ethyl acetate, collected by filtration, and dried to give 4-chloro-2-[2-ethoxy-3-(methylaminomethyl)phenoxy]benzonitrile fumarate (527 mg, 67%) as a white solid.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated overnight with ethyl acetate
  6. filtrationcollected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-648a42af66064baf852cde67161219c2
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276528B2

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