7-(benzyloxy)-4-chloro-6-Methoxyquinoline-3-carbonitrile synthesis

14synthesis methods

Product Name:7-(benzyloxy)-4-chloro-6-Methoxyquinoline-3-carbonitrile
CAS Number:214476-99-0
Molecular formula:C18H13ClN2O2
Molecular Weight:324.76

3-Quinolinecarboxamide, 4-chloro-6-methoxy-7-(phenylmethoxy)-

307353-92-0
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7-(benzyloxy)-4-chloro-6-Methoxyquinoline-3-carbonitrile

214476-99-0
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Yield:214476-99-0 99%

Reaction Conditions:

with trichlorophosphate at 110 - 120; for 22 h;

Steps:

1

A mixture of (5) (20.55g, 60 mmole) and phosphoryl chloride (250mL) was heated and stirred at 120°C for 4 hours when the starting material had dissolved. Heating and stirring was continued at 110°C for 18 hours. After cooling, the solution was evaporated to remove excess phosphoryl chloride. Last traces of phosphoryl chloride were removed by azeotroping with toluene. The residue was treated with ice and aqueous ammonia to remove acidity. The solid product was filtered off and dried in a vacuum oven to give a grey solid, 19.23g (99% yield). (This may also be prepared as described in WO 9843960)Mass Spectrum m/e 325 (M++H).

References:

EP1584619,2005,A1 Location in patent:Page/Page column 41-42