Sodium Carbonate → Methyl 6-amino-2-methyl-3-nitrobenzoate

HRID 1064092

Reaktionsgleichung

Reaktionsgleichung von HRID 1064092
[CH3:1][C:2]1[C:11]2[C:10](=[O:12])[O:9][C:8](=O)[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].NC1C=CC=C(C)C=1C(O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:8][O:9][C:10](=[O:12])[C:11]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([N+:14]([O-:16])=[O:15])[C:2]=1[CH3:1]

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 1512106-Methylanthranilic acidHCID 219011545-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

Produkt 1

HCID 15334532Methyl 6-amino-2-methyl-3-nitrobenzoateAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione (8 g, 36.0 mmol) prepared from 2-Amino-6-methyl-benzoic acid (Aldrich) as described by Abood, N. A., et al. (1997) Bioorganic & Med. Chem. Lett. 7: 2105-2108 and sodium carbonate (3.82, 36.0 mmol) were stirred in methanol (180 mL, 0.1 M) at 0° C. for 0.5 hours and then at ambient temperature for 3 hours. Strongly acidic ion-exchange resin (Dowex® 50 WX4-200) was added until neutral pH and the solution was filtered. The solvent was removed under reduced pressure and silica gel chromatography (60:40 hexane/ethyl acetate) afforded Intermediate 1(a) (6.59 g) in 87% yield.

Aufarbeitung

  1. additionStrongly acidic ion-exchange resin (Dowex® 50 WX4-200) was added until neutral pH
  2. filtrationthe solution was filtered
  3. customThe solvent was removed under reduced pressure and silica gel chromatography (60:40 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7492f88a602345f280d558575cc10673
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967198B2

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