N-methylhydroxylamine hydrochloride → 3-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl ester

HRID 1263605

Reaktionsgleichung

Reaktionsgleichung von HRID 1263605
C(OC(=O)C1C=C([C:12](=O)[N:13]([O:15]CC=C)C)C=C(N)C=1)C=C.[CH2:22]([O:25][C:26](=[O:46])[C:27]1[CH:28]=[C:29]([CH:40]=[C:41]([N+:43]([O-:45])=[O:44])[CH:42]=1)[C:30]([O:32]N1C(=O)CCC1=O)=O)[CH:23]=[CH2:24].Cl.CNO>ClCCl>[CH2:22]([O:25][C:26](=[O:46])[C:27]1[CH:42]=[C:41]([N+:43]([O-:45])=[O:44])[CH:40]=[C:29]([C:30](=[O:32])[N:13]([OH:15])[CH3:12])[CH:28]=1)[CH:23]=[CH2:24]

Komponenten

5

Edukt 3

HCID 77906N-methylhydroxylamine hydrochlorideHCID 229860995-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl esterHCID 229861413-amino-5(N-methyl-allyloxycarbamoyl)-benzoic acid allyl ester

Produkt 1

HCID 229861013-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Starting material (8(c)) was prepared as follows. A mixture of 7(b) (2.00 g; see Example 7), N-methylhydroxylamine hydrochloride (1.06 g) triethylamine (1.72 ml) and dichloromethane (60 ml.) was stirred at 5° for 30 minutes. It was then allowed to warm to ambient temperature and stirred for a further 16 hours. The reaction mixture was then poured directly onto a flash column eluting with ethyl acetate/hexane (50:50) to give 3-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl ester (8(a)) as a cream solid (1.43 g).

Aufarbeitung

  1. customwas prepared
  2. stirringstirred for a further 16 hours
  3. additionThe reaction mixture was then poured directly onto a flash column
  4. washeluting with ethyl acetate/hexane (50:50)

Quellen und Nachweise

ORD-Eintrag
ord-72f845aa0d474395a02b11627f42fb61
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541491B1

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