Hydrochloric Acid → Ethyl 2-benzoyl-6chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate

HRID 651007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 651007
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:11])[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1.Cl[C:32]([O:34][CH3:35])=[O:33].Cl>ClCCl>[C:17]([C:3]1[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[C:6]([C:2]=1[NH:1][C:32]([O:34][CH3:35])=[O:33])=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=2)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 183679133-Amino-2-benzoyl-4-chloro-1-(ethoxycarbonyl)indole

Produkt 1

HCID 69998691Ethyl 2-benzoyl-6chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of ethyl 3-amino-2-benzoyl-6-chloro-1H-indole-1-caboxylate (step 2, 1.5 g, 4.4 mmol) and pyridine (0.50 ml, 6.6 mmol) in dichloromethane (20 ml) was added methyl chloroformate (0.40 ml, 5.3 mmol) at room temperature. After stirring for 3 h, the mixture was poured into 2N aqueous HCl (20 ml) and extracted with dichloromethane (30 ml×2). The combined organic layers were dried (MgSO4) and concentrated to give 1.7 g (quant.) of the title compound as yellow amorphous solids.

Aufarbeitung

  1. extractionextracted with dichloromethane (30 ml×2)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e3ffb8b046704cd18cae7894ae1e9c42
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277878B1

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