ChemicalBook CAS DataBase List methyl 6-methoxypyridazine-3-carboxylate

methyl 6-methoxypyridazine-3-carboxylate synthesis

10synthesis methods

Product Name:methyl 6-methoxypyridazine-3-carboxylate
CAS Number:19194-96-8
Molecular formula:C7H8N2O3
Molecular Weight:168.15

67-56-1 Synthesis

67-56-1
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56434-28-7 Synthesis

56434-28-7
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methyl 6-methoxypyridazine-3-carboxylate

19194-96-8
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Yield:19194-96-8 100%

Reaction Conditions:

Stage #1: 6-methoxypyridazine-3-carboxylic acidwith thionyl chloride for 3 h;Heating / reflux;
Stage #2: methanol at 20;

Steps:

216.3 Step 3: 6-Methoxy-pyridazine-3- carboxylic acid methyl ester:

A solution of 6-chloro-pyridazine-3-carboxylic acid methyl ester in NaOMe in [MEOH] [(1M,] [10ML)] was refluxed on. [H20] was added and the mixture was extracted three times with DCM to give organic phase [I.] The combined organic phases I were dried and concentrated to give the title compound (40 mg, 10%). The water phase was acidified with concentrated hydrochloric acid and extracted three times with DCM to give organic phase II. The combined organic phases II were dried and concentrated to give 6-methoxy-pyridazine-3-carboxylic acid (LC-MS [(M++1)] : 155) (230 mg, 65%). A solution of 6-methoxy-pyridazine-3-carboxylic acid in thionyl chloride (6 ml) was refluxed for 3 h. The reaction was cooled to ambient temperature and evaporated to dryness. [MEOH] (10 ml) was added to the residue and the solution was stirred on at rt. Saturated [NAHC03] (aq) was added and the mixture was extracted three times with DCM. The combined organic phases were dried and concentrated to give the title compound (253 mg, 100%). LC-MS [(M++1)] : 169.

References:

WO2004/14881,2004,A2 Location in patent:Page 149

37972-69-3 Synthesis