Reaktion #50459

Reaktionsgleichung

5-nitro-6-methyl-2-acetylaminobenzoic acid

HCl

→

5-nitro-6-methyl-2-aminobenzoic acid

Ausbeute 48.0%

Lösungsmittel

NaOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux for two hours
2. 2
   Sonstigesitting in an ice bath
3. 3
   Sonstigeseparated out
4. 4
   workup.ADDITIONIn all, approximately 110 mL of 2N HCl was added
5. 5
   SonstigeThe collected yellow solid was dried in a vacuum oven for 3 hours at 75 degrees

Vorschrift

A solution of 10.2 g (43 mmoles) of 5-nitro-6-methyl-2-acetylaminobenzoic acid in 100 mL of 2M NaOH was heated to reflux for two hours. The resultant red solution was allowed to cool to near room temperature, then transferred to a beaker sitting in an ice bath. The solution was slowly acidified with 2N HCl to a pH of approximately 4-5 when a voluminous yellow solid separated out. In all, approximately 110 mL of 2N HCl was added. The collected yellow solid was dried in a vacuum oven for 3 hours at 75 degrees. 4.0 g (48% yield) 5-nitro-6-methyl-2-aminobenzoic acid was obtained. NMR(DMSO-d6): 2.45 (s,3H), 3.35(bs,2H), 6.68(d,1H,J=9.0 Hz), 7.86(d,1H,J=9.0 Hz). MS(m/z): 196(M+).

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