Bromination of compounds containing two aromatic nuclei. XVII. Bromination of some arylamides of 2-hydroxy-4-methylbenzoic acid (m-cresotic acid) was written by Patakoot, V. R.;Jadhav, G. V.. And the article was included in Journal of the Indian Chemical Society in 1956.Related Products of 49667-22-3 This article mentions the following:
The effect of a basic group, like arylamino, on the bromination in a group of arylamides (I) of 4,2-Me(HO)C6H3CO2H is reported. When mono-Br derivatives were formed, Br entered the acidic part; when a di-Br derivative was formed, Br entered the basic part also except in the cases of the m- and p-nitroanilides, where it entered the acidic part only. With liquid Br, higher Br derivatives, with Br in both nuclei, were obtained. The constitution of the Br derivatives was determined by hydrolyzing them with alkali or 80% H2SO4 and identifying the basic and acidic components. Bromination in AcOH was carried out in boiling solution in the same way as that of the arylamides (II) of 3,2-Me(HO)C6H3CO2H (loc. cit.) except in the cases of the anilide, o-nitroanilide, and p-anisidide, where the addition was made at 70-80°. The following compounds were prepared by this method (I used, cc. AcOH, cc. Br solution, Br compound formed, crystallization solvent, crystalline form, m.p. given) [in this abstract, Z = 4,2-Me(HO)C6H3CONH]: ZPh (III), 30, 3.0, 5-Br, dilute EtOH, white needles, 211-12°; ZC6H4-Me-2 (IV), 30, 2.6, 5-Br, dilute EtOH, white needles, 158-9°; III, 30, 6.0, 5-Br, dilute EtOH, white plates, 198-9°; ZC6H4Me-3 (V), 40, 5.2, 4′,5-Br2, dilute EtOH, white needles, 232-3°; ZC6H4Me-4 (VI), 30, 5.2, 5-Br, dilute EtOH, white needles, 245-6°; VI, 30, 10.4, 2′,3,5-Br3, dilute EtOH, white needles, 194-5°; ZC6H4NO2-2 (VII), 50, 3.0, 5-Br, dilute EtOH, yellow needles, 173-4°; ZC6H4NO2-3 (VIII), 80, 3.0, 5-Br, dilute EtOH, white needles, 244-5°; ZC6H4NO2-4 (IX), 140, 5.0, 3,5-Br2, AcOH, brown needles, 241-2°; ZC6H4OMe-2, 30, 8.0, 3,5,5′-Br3, AcOH, white needles, 208-9°; ZC6H4OMe-4 (X), 30, 2.5, 5-Br, dilute EtOH, white needles, 201-2°; X, 30, 5.0, 3′,5-Br2, dilute EtOH, white needles, 159-60°; ZC6H4OEt-4, 25, 2.5, 5-Br, dilute AcOH, white needles, 194-5°; ZC10H7-2 (XI) (C10H7 = naphthyl), 80, 5.0, 1′,5-Br2, dilute AcOH, white needles, 229-30°. Bromination with liquid Br was carried out at room temperature in the same way as with II, except with the o-nitroanilide and p-anisidide, where the mixture was boiled 4 hrs. on a boiling water bath and then left at room temperature The following compounds were prepared in this manner (I used, cc. Br, Br derivative formed, crystallization solvent, crystalline form, m.p. given) III, 3, 2′,3,4′,5-Br4, AcOH, white needles, 215-16°; IV, 3, 3,4′,5-Br3, AcOH, white needles, 210-11°; V, 3, 3,4′,5,6′. Br4, AcOH, white needles, 186-7°; VII, 3, 2′,3,4′,5-Br4, AcOH, yellow plates, 192-3°; VIII, 3, 3,5-Br2, dilute AcOH, white needles, 250-1°; IX, 3, 2′,3,4′,5-Br4, AcOH, dark brown needles, 226-7°; X, 3, 3,3′,5,6′-Br4, AcOH, white needles, 231-2°; XI, 3, 1′,3,5,6′-Br4, AcOH, white needles, 265-6°. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-4-methylbenzamide (cas: 49667-22-3Related Products of 49667-22-3).
2-Hydroxy-4-methylbenzamide (cas: 49667-22-3) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Related Products of 49667-22-3
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics