5-Aminopicolinic acid
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5-Aminopicolinic acid
structure -
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CAS No:
24242-20-4
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Formula:
C6H6N2O2
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Chemical Name:
5-Aminopicolinic acid
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Synonyms:
2-Pyridinecarboxylic acid,5-amino-;Picolinic acid,5-amino-;5-Amino-2-pyridinecarboxylic acid;5-Aminopicolinic acid;5-Aminopyridine-2-carboxylic acid
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CAS No:
Characteristics
76.2
0
Plates
1.4±0.1 g/cm3
218-219 °C
420°C at 760 mmHg
208.3±24.6 °C
1.649
0mmHg at 25°C
Safety Information
IRRITANT
NONH for all modes of transport
3
23/24/25-36/37/38-22
26-36/37/39-45-37
Xi,T,Xn
Irritant
P261-P305 + P351 + P338
H302-H315-H319-H335
|Warning|H302 (86.67%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
5-Aminopicolinic acid Use and Manufacturing
Intermediate 76. 5-aminopyridine-2-carboxylic acid A solution of 5-amino-2-cyanopyridine (10. Og, 83.9mmol) in sulfuric acid (50ml_) was placed in a high pressure vessel and heated to 90 °C for 2h. Then, water was added to the mixture (100ml_) and the reaction was heated to 100 °C for 2 additional hours. The obtained orange solution was poured over a mixture of ice and water and stirring was maintained for 15 min (a pale beige solid precipitated from the solution) and the solid obtained was filtered, washed with cold water and dried under vacuum overnight to afford the title compound (1 1 .7g, 100percent) LRMS (m/z): 139 (M+1 )+Synthesis of compound 206.2. The solution of 206.1 (4.0g, 33.61mmol, l .Oeq) in concentrated HA mixture of 5-aminopicolinic acid (159 mg, 1.1 mmol), tert-butyl (2-amino-5- fluorophenyl)carbamate (69, 248 mg, 1.1 mmol), triethylamine (333 mg, 3.3 mmol) in dimethylformamide (2.0 mL) was flushed with argon, and stirred at r.t. for 12 hours. The reaction mixture extracted with ice water (20.0 mL) and ethyl acetate (5.0 mL x 3). The combined organic extracts were washed with 2M HCl (aq) (5.0 mL), NaHCO3 (Sat) (25.0 mL). The combined organic layers were dried over Na2SO4 The crude product was purified with flash column chromatography on silica gel, and using 20percent Ethyl acetate/Hexanes to afford the 72 [tert-butyl(2-(5-aminopicolinamido)-5-fluorophenyl)carbamate]. The yield is 72percent, and as off white solid.: NMR (DMSO, 500 MHz): delta 1.49 (s, 9H), 6.11 (s, 2H), 7.02-7.07 (m, 2H), 7.14- 7.16 (m, 1H), 7.81 (d, 1H, J= 8.5 Hz), 7.87-7.90 (m, lH), 7.93 (s, 1H), 9.09 (s, 1H), 10.10 (s, 1H).
A useful synthetic intermediate
Computed Properties
Molecular Weight:138.12
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:138.042927438
Monoisotopic Mass:138.042927438
Topological Polar Surface Area:76.2
Heavy Atom Count:10
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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