ChemicalBook CAS DataBase List ISOCARBOXAZID (200 MG)

ISOCARBOXAZID (200 MG) synthesis

4synthesis methods

Product Name:ISOCARBOXAZID (200 MG)
CAS Number:59-63-2
Molecular formula:C12H13N3O2
Molecular Weight:231.25

Isocarboxazid, 2-benzylhydrazid-5-methyl-3-isoxazolecarboxylate (7.2.6), can be synthesized from acetylacetone, which on nitrosation with nitrous acid gives 5- methyl-isoxazol-3-carboxylic acid (7.2.2). Esterification of this product gives the ethyl ester of 5-methyl-isoxazol-3-carboxylic acid (7.2.3). The synthesized ester (7.2.3) is further reacted with benzylhydrazine, to give isocarboxazide (7.2.6), or with hydrazine, which forms 5-methyl-isoxazol-3-carboxylic acid hydrazide (7.2.4). Reacting the latter with benzaldehyde gives hydrazone (7.2.5), which is further reduced to the isocarboxazide (7.2.6) [46,47].

19788-35-3
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20570-96-1 Synthesis

20570-96-1
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59-63-2
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$27.00/5mg

Yield:59-63-2 93%

Reaction Conditions:

with triethylamine in n-heptane at 35;Temperature;

Steps:

1.C Example 1Preparation of N’-benzyl-5-methylisoxazole-3-carbohydrazide ( Isocarboxazid)
A reactor was charged at room temperature with methyl 5-methylisoxazole-3-carboxylate (30g), benzylhydrazine dihydrochloride (62.8 g, potentiometric assay of 99%) and n-heptane(450 ml). To the suspension was added slowly with a dropping funnel triethylamine (65.6 g).At the end of the addition the temperature was adjusted to about 35°C and maintained at thattemperature overnight. An in-process control sample taken after about 16 hours showed only 0.2% of methyl 5-methylisoxazole-3-carboxylate. The suspension was cooled to 20°C and water (120 ml) was added slowly with a dropping funnel. The suspension was filtered and washed with water (2 x 60 ml) and n-heptane (2 x 60 ml). The product was dried undervacuum at 50°C and Isocarboxazid (45.5 g, molar yield of 93%, purity by HPLC 99.1%) was obtained as white solid.

References:

LUNDBECK PHARMACEUTICALS ITALY S.P.A.;DE FAVERI, Carla;HUBER, Florian, Anton, Martin;ANTOLINI, Nicola WO2017/21246, 2017, A1 Location in patent:Page/Page column 10; 11; 12

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91397-11-4 Synthesis