4-Chlorobenzoic Acid → Methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-aminobenzoate

HRID 2417481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2417481
[CH2:1]([O:3][C:4]([CH2:6][NH:7][CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[C:12]([O:14][CH3:15])=[O:13])=[O:5])[CH3:2].C(N(CC)CC)C.[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1.[H][H]>ClCCl.C(OCC)(=O)C.[Pd]>[Cl:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([CH2:2][CH2:1][O:3][C:4]([CH2:6][NH:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[NH2:19])[C:12]([O:14][CH3:15])=[O:13])=[O:5])=[O:35])=[CH:32][CH:31]=1

Komponenten

8

Edukt 4

HCID 63184-Chlorobenzoic AcidHCID 8471TriethylamineHCID 22632382Methyl 3-[(ethoxycarbonylmethylamino)methyl]-4-nitrobenzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 69892547Methyl 3-[((4-chlorobenzoyl)ethoxycarbonylmethylamino)methyl]-4-aminobenzoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2.2 g (6.14 mmol) of methyl 3-[(ethoxycarbonylmethylamino)-methyl]-4-nitrobenzoate was dissolved in 50 ml of dichloromethane. 4 mg (0.023 mmol) of 2-chloro-1,3-dimethylimidazonium chloride, 1.29 ml (9.2 mmol) of triethylamine and 1.16 g (7.3 mmol) of 4-chlorobenzoic acid were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 20 ml of ethyl acetate. 200 mg of 10% palladium/carbon was added to the obtained solution and they were stirred in the presence of hydrogen at room temperature for 5 hours. The reaction mixture was filtered through Celite and the solvent was evaporated to obtain the crude product.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-bf48037024d24fb3aa3fcfdd82d810bd
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06825191B2

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