| Identification | Back Directory | [Name]
4-PYRIDINAMINE, 2-CHLORO-5-METHYL- | [CAS]
79055-62-2 | [Synonyms]
2-Chloro-5-Methyl-4-pyridinaMine
2-Chloro-4-amino-5-methylpyridine
4-aMino-2-chloro-5-Methylpyridine
2-Chloro-5-methyl pyridine-4-amine
4-PYRIDINAMINE, 2-CHLORO-5-METHYL-
2-Chloro-5-Methyl-pyridin-4-ylaMine
2-Chloro-5-methylpyridin-4-amine 98% | [Molecular Formula]
C6H7ClN2 | [MDL Number]
MFCD11977435 | [MOL File]
79055-62-2.mol | [Molecular Weight]
142.59 |
| Chemical Properties | Back Directory | [Melting point ]
115℃ | [Boiling point ]
310.1±37.0 °C(Predicted) | [density ]
1.260±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
powder | [pka]
5.11±0.42(Predicted) | [color ]
Off-white | [InChI]
InChI=1S/C6H7ClN2/c1-4-3-9-6(7)2-5(4)8/h2-3H,1H3,(H2,8,9) | [InChIKey]
CJGKOPNIXJWHKF-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C(C)C(N)=C1 |
| Hazard Information | Back Directory | [Uses]
2-Chloro-5-methylpyridin-4-amine is a key intermediate in phenelzine. Phenelzine is a novel nonsteroidal mineralocorticoid receptor antagonist that not only demonstrates improved safety and efficacy in treating heart failure and chronic kidney disease, but also plays an important role in the treatment of atrial fibrillation and myocardial infarction. | [Synthesis]
2-chloro-5-methylpyridin-4-amine was synthesised by reaction with 2-chloro-5-methyl-4-nitropyridine 1-oxide. The synthesis steps are as follows:
A glass pressure reactor with cross-beam stirrer was charged under argon with 29 g (153.788 mmol) of 2-chloro-5-methyl-4-nitro-1-oxidopyridin-1-ium and 2.9 g of hydrogenation catalyst (0.8% Pt and 0.6% Mo on activated carbon (D505A-105 0.8% Pt+0.6% Mo on carbon powder, BASF) and 320 ml of ethanol were added. The reactor was closed and inertized three times, each time with 3 bar argon overpressure. Hydrogenation was then carried out for 20 hours at 30℃, under a 3 bar hydrogen overpressure (conversion >98%). The reactor was inertized with argon and the reaction solution filtered through 10 g of kieselguhr. The filtrate was concentrated to dryness under reduced pressure. Yield: 23.0 g (quantitative, product still contained ethanol), purity: 97.5% (HPLC) (0051) MS (EIpos): m/z=143 [M+H]+ (0052) 1H-NMR (300 MHz, DMSO-d6): δ=1.96 (s, 3H), 6.16 (br s, 2H), 6.50 (s, 1H), 7.68 (s, 1H) In an analogous manner, a conversion of approx. 98% was achieved with a catalyst consisting of 0.8% Pt and 0.3% Mo on activated carbon. Use of 1% Pt+2% V on activated carbon achieved a conversion of approx. 87%.
 | [storage]
Keep in dark place, Inert atmosphere, 2-8°C
| [References]
[1] Patent: CN103193704, 2016, B. Location in patent: Paragraph 0025; 0035-0039
[2] Patent: WO2005/100342, 2005, A1. Location in patent: Page/Page column 24; 39
[3] Patent: WO2003/91246, 2003, A1. Location in patent: Page/Page column 49 |
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