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Prominently, it is the final intermediate in the industrial synthesis of paracetamol. Treating 4-aminophenol with acetic anhydride gives paracetamol: [8] [9] [10] It is a precursor to amodiaquine, mesalazine, AM404, parapropamol, B-86810 & B-87836 (c.f. WO 2001042204 ). 4-Aminophenol converts readily to the diazonium salt. [11]
Acetanilide can be produced by reacting acetic anhydride with aniline: [7]. C 6 H 5 NH 2 + (CH 3 CO) 2 O → C 6 H 5 NHCOCH 3 + CH 3 COOH. The preparation used to be a traditional experiment in introductory organic chemistry lab classes, [8] but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially ...
Paracetamol, [a] or acetaminophen, [b] is a non-opioid analgesic and antipyretic agent used to treat fever and mild to moderate pain. [13] [14] [15] It is a widely available over-the-counter drug sold under various brand names, including Tylenol and Panadol. Paracetamol relieves pain in both acute mild migraine and episodic tension headache.
An industrial synthesis of paracetamol developed by Hoechst–Celanese involves the conversion of a methyl ketone to an acetanilide via a Beckmann rearrangement. [15] The thermal rearrangement that occurs in the synthesis of ketamine was claimed to be a Beckmann rearrangement according to: url.
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) [6] is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group ( −C 6 H 5 ) attached to an amino group ( −NH 2 ), aniline is the simplest aromatic amine .
The reaction was first used by Antoine Béchamp to reduce nitronaphthalene and nitrobenzene to naphthylamine and aniline, respectively. [3] The Béchamp reduction is broadly applicable to aromatic nitro compounds. [4] [5] Aliphatic nitro compounds are however more difficult to reduce, often remaining as the hydroxylamine. Tertiary aliphatic ...
An alternative mechanism is based on the aniline and the aldehyde forming at first the Schiff base upon water elimination. The subsequent reaction with the enol form of pyruvic acid ( 1 ) leads to the formation of the above-mentioned aniline derivative ( 3 ) followed by the above-described reaction mechanism: [ 4 ]
Aniline reacts with acyl chlorides or carboxylic anhydrides to give anilides. For example, reaction of aniline with acetyl chloride provides acetanilide ( CH 3 −CO−NH−C 6 H 5 ). At high temperatures, aniline and carboxylic acids react to give anilides.