Methylamine → 4-Chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate

HRID 1243688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1243688
[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][C:14]([CH:17]=O)=[C:13](OC)[CH:12]=2)[CH:3]=1.CN.[C:23]([BH3-])#[N:24].[Na+].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31]>C(OCC)(=O)C.C(O)(=O)C.CO>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]/[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:12]=[CH:13][C:14]([CH2:17][NH:24][CH3:23])=[CH:15][C:16]=2[O:31][CH3:30])[CH:3]=1

Komponenten

7

Edukt 4

HCID 6329MethylamineHCID 444972Fumaric AcidHCID 5003444Sodium cyanoborohydrideHCID 219303894-Chloro-2-(4-formyl-3-methoxy-phenoxy)-benzonitrile

Produkt 1

HCID 219303444-Chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarateAusbeute 109,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 10129899Acetic acid methanolLösungsmittel

Versuchsvorschrift

4-Chloro-2-(4-formyl-3-methoxy-phenoxy)-benzonitrile (0.93 g, 3.2 mmol), methylamine (2M in methanol, 4.8 ml, 9.6 mmol) and sodium cyanoborohydride (0.22 g, 3.6 mmol) were stirred at ambient temperature in a 1% acetic acid/methanol solution (125 ml) for 20 h. The solvent was removed in vacuo. The residue was treated with 10% aqueous sodium carbonate and extracted with ethyl acetate. Fumaric acid (0.40 g, 3.4 mmol) was added to the separated ethyl acetate layer and the solvent removed in vacuo. The residue was triturated with ethyl acetate overnight, filtered and dried to give 4-chloro-2-(2-methoxy-4-methylaminomethyl-phenoxy)-benzonitrile fumarate (782 mg, 58%) as a white solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-c365485da2b144a3ae07af0eb4f39e27
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07119122B2

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