8-Methoxyquinoline-4-carboxylic acid synthesis
- Product Name:8-Methoxyquinoline-4-carboxylic acid
- CAS Number:148887-46-1
- Molecular formula:C11H9NO3
- Molecular Weight:203.19
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Yield:148887-46-1 62%
Reaction Conditions:
with sulfuric acid;iodine in water;glycerol;
Steps:
1 Step 1:
Step 1:
Preparation of 8-methoxy-quinoline-5-carboxylic acid AC001 (Org. Lett. 2005, 17, 3673)
Reflux a mixture of 25 g 3-amino-4-methoxybenzoic acid, 0.72 g iodine, 20.8 g glycerol and 50 mL conc. H2SO4 for 2.5 hours (internal temperature at ?135° C.).
After cooling to room temperature, 250 mL of water was added, followed by 90 mL of 28% aq. NH4OH to pH ?10.
The mixture was then treated with charcoal, filtered and the filtrate was adjusted to pH ?4 with 70 mL glacial acetic acid where upon the solids product precipitated out.
The solids product was filtered, washed with water, dried under vacuum at 50° C. over night to give 18.8 g (62%) of 8-methoxy-quinoline-5-carboxylic acid AC001.
1H NMR (400 MHz DMSO-d6) δ (ppm): 12.97 (bs, 1H), 9.41 (dd, 1H), 8.89 (dd, 1H), 8.30 (d, 1H), 7.67 (dd, 1H), 7.26 (d, 1H), 4.04 (s, 3H).
References:
US2014/94487,2014,A1 Location in patent:Page/Page column
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148887-46-1
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