6-Quinolinecarboxylic acid synthesis
- Product Name:6-Quinolinecarboxylic acid
- CAS Number:10349-57-2
- Molecular formula:C10H7NO2
- Molecular Weight:173.17
150-13-0
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56-81-5
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10349-57-2
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Yield:10349-57-2 95%
Reaction Conditions:
with ferrous(II) sulfate heptahydrate;sulfuric acid;boric acid;4-nitro-benzoic acid at 140;
Steps:
73.1
Step 1. Quinoline-6-carboxylic acid Into a 500-mL 3-necked round-bottom flask, was placed 4-aminobenzoic acid (13.7 g, 100.00 mmol, 1.00 equiv), 4-nitrobenzoic acid (10.7 g, 64.07 mmol, 0.64 equiv), boric acid (5.9 g), FeSO4.7H2O (6.4 g), glycerol (38 mL), and concentrated sulfuric acid (18 mL). The resulting solution was stirred overnight at 140° C. The reaction mixture was cooled. The pH value of the solution was adjusted to 10 with sodium hydroxide (10%). The resulting solution was extracted with 2*100 mL of ethyl acetate and the aqueous layers were combined. The pH value of the aqueous layers was adjusted to pH 6 with conc. hydrochloric acid. The solids were collected by filtration. The resulting solution was diluted with 200 mL of methanol and the resulting solids were collected by filtration. The solid was dried to afford 17.3 g (95%) of quinoline-6-carboxylic acid as a dark-grey solid. LC-MS: (ES, m/z):174 [M+H]+
References:
BIOENERGENIX US2012/277224, 2012, A1 Location in patent:Page/Page column 82
91-62-3
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10349-57-2
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38896-30-9
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10349-57-2
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5332-25-2
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124-38-9
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10349-57-2
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5382-49-0
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10349-57-2
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