ChemicalBook CAS DataBase List 3-METHYL-4-NITROBENZONITRILE

3-METHYL-4-NITROBENZONITRILE synthesis

5synthesis methods

Product Name:3-METHYL-4-NITROBENZONITRILE
CAS Number:96784-54-2
Molecular formula:C8H6N2O2
Molecular Weight:162.15

3113-71-1 Synthesis

3113-71-1
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$6.00/25g

70-55-3 Synthesis

70-55-3
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$6.00/100g

96784-54-2
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$7.00/250mg

Yield: 35.9 g (23 %)

Reaction Conditions:

with pyridine;phosphorus pentachloride;trichlorophosphate in dichloromethane

Steps:

1.A Part A
Part A Preparation of the intermediate 4-nitro-3-tolunitrile, represented by the formula: A mixture of PCl₅ (200 g, 0.96 mole) and p-toluene sulfonamide (90 g, 0.52 mole) was treated with 3-methyl-4-nitrobenzoic acid (82 g, 0.44 mole). The reaction was stirred at room temperature for 1 hour at which time it was heated to 140°C and the POCl₃ (150 ml) distilled from the mixture. The reaction was cooled to 5°C, pyridine (200 ml) was carefully added and the mixture allowed to stand overnight. The reaction was carefully diluted to 1 L with H₂O and the mixture stirred for 3 hours. The brown solid was filtered, washed with H₂O and triturated with 5 N aqueous NaOH. The remaining solid was filtered, washed with H₂O and dried to afford 60.0 g of a powder. The solid was stirred in 1200 ml CH₂Cl₂ and filtered. The supernatant was evaporated in vacuo and the residue recrystallized from EtOH to give 35.9 g (23 %) of 4-nitro-3-tolunitrile. MS(FD), m/e 162 (M+).

References:

ELI LILLY AND COMPANY EP655439, 1995, A2