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ChemicalBook CAS DataBase List 3-CYANO-5-NITROBENZOIC ACID

3-CYANO-5-NITROBENZOIC ACID synthesis

4synthesis methods
-

Yield:98556-65-1 94%

Reaction Conditions:

with potassium cyanide;sodium nitrite in hydrogenchloride;water;

Steps:

21 3-Cyano-5-nitrobenzoic acid

3-Amino-5-nitrobenzoic acid (3.64 g, 20 mM) was dissolved in concentrated hydrochloric acid (20 ml), diluted with water (75 ml), cooled to 0°, and added over 30 minutes to a solution of NaNO2 (1.38 g, 20 mM) in water (10 ml). The pH was adjusted to 6.2 with saturated Na2 CO3 solution. A mixture of CuSO4.5H2 O (10 g, 42 mM) in water (40 ml) and KCN (10 g, 154 mM) in water (20 ml) was heated to 65°, the solution of diazonium salt added over 15 minutes, and the mixture refluxed for 40 minutes. After cooling, and acidifying with 2M hydrochloric acid, the organics were extracted into ethyl acetate (2*200 ml). The combined extracts were washed with aqueous NaH2 PO4, water, brine, and dried over Na2 SO4. Evaporation gave 3-cyano-5-nitrobenzoic acid (3.6 g, 94%). Nmr (DMSO-d6): δ8.69 (t, 1H); 8.80 (t, 1H); 8.97 (t, 1H).

References:

US5478820,1995,A