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| | 2-Amino-3-benzyloxypyridine Basic information |
| | 2-Amino-3-benzyloxypyridine Chemical Properties |
| Melting point | 92-94 °C (lit.) | | Boiling point | 337.96°C (rough estimate) | | density | 1.1131 (rough estimate) | | refractive index | 1.6660 (estimate) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 8.40±0.10(Predicted) | | form | Crystalline Powder | | color | Green to brown | | BRN | 392674 | | InChI | InChI=1S/C12H12N2O/c13-12-11(7-4-8-14-12)15-9-10-5-2-1-3-6-10/h1-8H,9H2,(H2,13,14) | | InChIKey | NMCBWICNRJLKKM-UHFFFAOYSA-N | | SMILES | C1(N)=NC=CC=C1OCC1=CC=CC=C1 | | CAS DataBase Reference | 24016-03-3(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Pyridinamine, 3-(phenylmethoxy)-(24016-03-3) |
| | 2-Amino-3-benzyloxypyridine Usage And Synthesis |
| Chemical Properties | Brown crystalline powder | | Uses | 2-Amino-3-benzyloxypyridine is used in preparation of pyridinyl/pyridazinyloxymethyl substituted Raf kinase inhibitors. | | Uses | 2-Amino-3-benzyloxypyridine was used in the synthesis of 1-acetyl-2-[2-(3-benzyloxypyridinyl)]iminoimidazolidine. | | General Description | 2-Amino-3-benzyloxypyridine on condensation with diethyl ethoxymethylene malonate affords 9-benzyloxy-3-ethoxycarbonylpyrido[1,2-a]pyrimidin-4-one. | | Biochem/physiol Actions | 2-Amino-3-benzyloxypyridine is an inhibitor of mitogen-activated protein kinase p38α activity. | | Synthesis | At a temperature lower than 40°C, 48L of deionized water was added to a 300L stainless steel reactor, and 48kg of sodium hydroxide was added under slow stirring until completely dissolved. Subsequently, 16 kg of 2-amino-3-hydroxypyridine, 1.6 kg of tetrabutylammonium bromide, and 17.92 L of benzyl chloride were added sequentially to the sodium hydroxide solution. The reaction mixture was heated to 70~75°C and kept at this temperature for 6 hours. When the reaction was completed, stirring was stopped and the mixture was left to stratify. The aqueous phase was extracted with toluene (20L x 3) and the combined organic phases were washed with pure water (30L x 2). The organic phase was concentrated until a large amount of solid precipitated, followed by crystallization at 0~5°C and stirring for 2 hours. Upon completion of crystallization, centrifugation was performed and the filter cake was washed with 3.2 L of pre-cooled toluene. Finally, it was dried under vacuum at 50~55°C for 3 h to give 22.5 kg of bright yellow solid Intermediate II (2-amino-3-benzyloxypyridine) in 77.3% molar yield and 99.53% purity. | | References | [1] Chemistry Letters, 2006, vol. 35, # 3, p. 270 - 271
[2] Synthesis, 1981, # 12, p. 971 - 973
[3] Patent: CN107311998, 2017, A. Location in patent: Paragraph 0035-0036
[4] Journal of Chemical Research, Miniprint, 1986, # 11, p. 3368 - 3390
[5] Patent: CN103570683, 2018, B. Location in patent: Paragraph 0927; 0928; 0930; 0931 |
| | 2-Amino-3-benzyloxypyridine Preparation Products And Raw materials |
| Raw materials | 2-Amino-3-hydroxypyridine-->TETRABUTYLAMMOMIUM BROMIDE-->Sodium hydroxide-->Benzyl chloride-->Benzyl bromide | | Preparation Products | 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one-->8-(benzyloxy)-2-methylimidazo[1,2-a]pyridine-->8-BENZYLOXY-2-METHYL-IMIDAZO[1,2-A]PYRIDINE-3-CARBOXYLIC ACID ETHYL ESTER-->[1,2,4]Triazolo[1,5-a]pyridin-2-amine, 8-(phenylmethoxy)- |
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