1125-80-0 Usage
Description
The metabolites of 3-methylisoquinoline were separated by adsorption and reversed-phase high-performance liquid chromatography (HPLC).
Uses
3-Methylisoquinoline was used to prepare 3-aminoisoquinoline.
Preparation
Benzylamine (9.18 mL, 84.0 mmol) and 1,1-dimethoxypropan-2-one (9.95 mL, 84.0 mmol) were added to dichloromethane (350 mL) at room temperature. Sodium triacetoxyborohydride (25 g, 118 mmol) was added to the reaction mixture in one portion. The reaction was stirred at room temperature overnight. The reaction mixture was then diluted with 2.5% sodium bicarbonate (250 mL) and mixed for 30 minutes, becoming biphasic. The organic layer was discarded. The aqueous layer was basified to pH 14 using concentrated sodium hydroxide. The basified aqueous solution was washed three times with ethyl acetate and the organic layers were kept and combined. Then, the resulting solution was washed with 5% sodium chloride solution three times. The organic layers were combined and dried over sodium sulfate. The resulting solution was evaporated to a yellow oil, which was found to be N-benzyl-1,1-dimethoxypropan-2-one. The oil (2.62 g, 12.5 mmol) was added dropwise to chlorosulfonic acid (8.35 mL, 125 mmol) over ice. A few milliliters of dichloromethane was used to rinse the oil from its reaction flask and the oil dissolved in dichloromethane was also added to the chlorosulfonic acid flask over ice. The reaction mixture was placed over boiling water for 5 minutes with a condenser to evaporate the solvent used to rinse the N-benzyl-1,1-dimethoxypropan-2-one out of its previous flask while not letting any water vapor enter the flask before the reaction mixture was fully heated. Then, the reaction mixture was placed in the boiling water for 10 minutes without a condenser to allow methanol, a side-product of the reaction, to evaporate out of the flask and drive the reaction forward. After cooling, the reaction mixture was quenched with ice and then basified to pH 14 with concentrated sodium hydroxide. The mixture was washed with dichloromethane three times. The organic layers were combined and dried using magnesium sulfate. The resulting solution was evaporated to solid 3-methylisoquinoline (average percent yield: 2-5%) and the structure was confirmed with GC-MS and NMR.
Synthesis Reference(s)
Tetrahedron Letters, 26, p. 3959, 1985 DOI: 10.1016/S0040-4039(00)98697-0Chemical and Pharmaceutical Bulletin, 35, p. 4964, 1987 DOI: 10.1248/cpb.35.4964
Check Digit Verification of cas no
The CAS Registry Mumber 1125-80-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,2 and 5 respectively; the second part has 2 digits, 8 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1125-80:
(6*1)+(5*1)+(4*2)+(3*5)+(2*8)+(1*0)=50
50 % 10 = 0
So 1125-80-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H9N/c1-8-6-9-4-2-3-5-10(9)7-11-8/h2-7H,1H3
1125-80-0Relevant articles and documents
Synthesis of Isoquinolines from Indenes
Miller, R. Bryan,Frincke, James M.
, p. 5312 - 5315 (1980)
A general procedure for the synthesis of isoquinolines from appropriately substituted indenes is described.Ozonolysis of the indenes followed by reductive workup gives intermediate homophthalaldehydes which are treated with ammonium hydroxide to give the isoquinolines.This "one-pot", three-step reaction sequence was applied to the formation of all of the mono-C-methyl-substituted isoquinolines in a regiospecific manner.The procedure is applicable to both electron-withdrawing and electron-donating substituents on the indene system.In this manner the 6- and 7-nitro-,-bromo-, and -iodoisoquinolines were prepared.
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.
Potassium tert-Butoxide-Promoted Acceptorless Dehydrogenation of N-Heterocycles
Liu, Tingting,Wu, Kaikai,Wang, Liandi,Yu, Zhengkun
supporting information, p. 3958 - 3964 (2019/08/01)
Potassium tert-butoxide-promoted acceptorless dehydrogenation of N-heterocycles was efficiently realized for the generation of N-heteroarenes and hydrogen gas under transition-metal-free conditions. In the presence of KOtBu base, a variety of six- and five-membered N-heterocyclic compounds efficiently underwent acceptorless dehydrogenation to afford the corresponding N-heteroarenes and H2 gas in o-xylene at 140 °C. The present protocol provides a convenient route to aromatic nitrogen-containing compounds and H2 gas. (Figure presented.).
