42398-73-2 Usage
Chemical Properties
Light beige powder
Uses
6-Methylisoquinoline (cas# 42398-73-2) is a useful reagent for the green preparation of polyfluoroarylated heterocyclic compounds.
Preparation
A benzene solution (50 ml, CAUTION) of equimolar amounts of p-tolualdehyde (8.4 g, 0.07 mol) and aminoacetaldehyde dimethyl acetal (7.35 g, 0.07 mol) is refluxed overnight into a Dean and Stark trap. The solution is evaporated in vacuo and then twice evaporated again with added benzene and the viscous oil dissolved in dry tetrahydrofuran. This solution is cooled to - 10 °C and 1 equivalent of ethyl chloroformate (7. 1 ml, 0.07 mol) is added with rapid stirring and the mixture stirred for a further 5 minutes. The cooling bath is removed and 1.2 equivalents of trimethyl phosphite ( 10.5 ml, 0.09 mol) is added with stirring. The solution is stirred at room temperature for 1 5 hours and then evaporated t o an oil. The oil is then re-evaporated twice with added toluene to remove traces of trimethyl phosphite. The oil is dissolved in dry dichloromethane, 6 equivalents of titanium(1v) chloride (50 ml, 0.45 mol) is added and the solution refluxed for 36 hours under a drying tube. The cooled solution is shaken with 1 equivalent of aqueous sodium hydroxide solution to neutrality, whereupon titanium(1v) oxide precipitates as a white solid. The filtered organic layer is extracted with 3 M hydrochloric acid, and the extract is washed with dichloromethane, basified strongly with aqueous alkali, and extracted with dichloromethane. This organic extract is dried over anhydrous sodium sulphate and evaporated to afford 6-methylisoquinoline (yield 7 1 %, m.p. 88 °C).
Synthesis Reference(s)
The Journal of Organic Chemistry, 48, p. 3344, 1983 DOI: 10.1021/jo00167a043
Check Digit Verification of cas no
The CAS Registry Mumber 42398-73-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,2,3,9 and 8 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 42398-73:
(7*4)+(6*2)+(5*3)+(4*9)+(3*8)+(2*7)+(1*3)=132
132 % 10 = 2
So 42398-73-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H9N/c1-8-2-3-10-7-11-5-4-9(10)6-8/h2-7H,1H3
42398-73-2Relevant articles and documents
Cu(II)-Catalyzed Construction of Heterobiaryls using 1-Diazonaphthoquinones: A General Strategy for the Synthesis of QUINOX and Related P,N Ligands
Biswas, Aniruddha,Pan, Subarna,Samanta, Rajarshi
supporting information, p. 1631 - 1636 (2022/03/14)
An efficient and straightforward method was developed for the synthesis of heterobiaryls using easily available N-oxides and diazonaphthoquinones under cheap Cu(II) catalysis. The developed method offered QUINOX and related congeners in a simple manner. A wide scope of important heterobiaryls was achieved with high site selectivity. The synthesized naphthols were transformed into the privileged related P,N ligands. Suitable resolution methods can directly afford the corresponding axially chiral heterobiaryls.
ISOQUINOLINE-5-CARBOXAMIDE DERIVATIVE HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASE
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Paragraph 0072, (2015/06/03)
A compound selected from the group consisting of an isoquinoline-5-carboxamide derivative of formula (I), a pharmaceutically acceptable salt, an isomer, a hydrate and a solvate thereof is effective for the prevention or treatment of diseases associated with abnormal cell growth, which are caused by abnormal activation of a protein kinases.
THIENO[3,2-D]PYRIMIDINE DERIVATIVES HAVING INHIBITORY ACTIVITY FOR PROTEIN KINASES
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Paragraph 0216; 0217, (2015/01/06)
Provided are a thieno[3,2-d]pyrimidine derivative of formula (I) or a pharmaceutically acceptable salt thereof having inhibitory activity for protein kinase, and a pharmaceutical composition comprising same for prevention and treatment of abnormal cell growth diseases.
