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

HRID 1977353

Reaktionsgleichung

Reaktionsgleichung von HRID 1977353
[CH2:1]([O:4][C:5](=[O:25])[C:6]1[CH:7]=[C:8]([CH:19]=[C:20]([N+:22]([O-:24])=[O:23])[CH:21]=1)[C:9]([O:11]N1C(=O)CCC1=O)=O)[CH:2]=[CH2:3].Cl.[CH3:27][NH:28][OH:29]>ClCCl>[CH2:1]([O:4][C:5](=[O:25])[C:6]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[C:8]([C:9](=[O:11])[N:28]([OH:29])[CH3:27])[CH:7]=1)[CH:2]=[CH2:3]

Komponenten

4

Edukt 2

HCID 77906N-methylhydroxylamine hydrochlorideHCID 229860995-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester

Produkt 1

HCID 229861013-(N-methyl-hydroxycarbamoyl)-5-nitro-benzoic acid allyl esterAusbeute 88,9 %

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° or 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-8eaf5aa4cfe0494f8a6de93fa605939b
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232338B1

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