83491-16-1

Basic information

• Product Name: 2(1H)-Isoquinolinecarboxamide, 3,4-dihydro-N-phenyl-
• CAS NO: 83491-16-1
• Molecular Formula: C16H16N2O
• Molecular Weight: 252.316
• Mol File: 83491-16-1.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 2(1H)-Isoquinolinecarboxamide, 3,4-dihydro-N-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(1H)-Isoquinolinecarboxamide, 3,4-dihydro-N-phenyl-(83491-16-1)
• EPA Substance Registry System: 2(1H)-Isoquinolinecarboxamide, 3,4-dihydro-N-phenyl-(83491-16-1)

Safety Data

• Hazardous Substances Data: 83491-16-1(Hazardous Substances Data)

Upstream product

• 199480-42-7 1,2,3,4-tetrahydroisoquinolin-2-ylcarbonyl chloride 
• 62-53-3 aniline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 3422-02-4 N-(benzyloxycarbonyl)aniline 
• 42864-21-1 2,2,2-trichloroethyl-N-phenyl carbamate 
• 501-82-6 N-phenylcarbamic acid 
• 67-64-1 acetone 
• 414883-79-7 2-[(4-dimethylaminophenyl)methyl]-1,2,3,4-tetrahydroisoquinoline 
• 375831-25-7 2-[(2,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline 
• 173034-82-7 2-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline 
• 59325-13-2 N-ethoxycarbonyl-1,2,3,4-tetrahydroisoquinoline 
• 82342-56-1 N-benzoyl-1,2,3,4-tetrahydroisoquinoline 
• 13605-95-3 N-benzyl-1,2,3,4-tetrahydroisoquinoline 
• 1612-65-3 2-methyl-1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

Synthesis of ureas in the bio-alternative solvent Cyrene

Cyrene as a bio-alternative solvent: a highly efficient, waste minimizing protocol for the synthesis of ureas from isocyanates and secondary amines in the bio-available solvent Cyrene is reported. This method eliminated the use of toxic solvents, such as

A Facile and Efficient Method for the Formation of Unsymmetrical Ureas Using DABAL-Me3

A practical synthetic method for the formation of unsymmetrical-substituted ureas is described. The synthesis of the unsymmetrical ureas was readily performed from 2,2,2-trichloroethyl carbamate compounds by treatment of amines with bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane (DABAL-Me3). Using this reaction protocol, various trisubstituted and tetrasubstituted ureas were synthesized in high yields. This study offers a promising approach for the facile synthesis of a variety of unsymmetrical ureas from 2,2,2-trichloroethyl carbamates.

Debenzylation of tertiary amines using phosgene or triphosgene: An efficient and rapid procedure for the preparation of carbamoyl chlorides and unsymmetrical ureas. Application in carbon-11 chemistry

Efficient and rapid preparations of carbamoyl chlorides and unsymmetrical ureas from tertiary amines and phosgene or its safe equivalent triphosgene [bis(trichloromethyl)carbonate, BTC] are described. First, the reaction of stoichiometric amounts of phosgene with secondary amines was revisited, and it was shown that the formation of carbamoyl chlorides in high yields required careful adjustments of experimental conditions and the use of pyridine as an HCl scavenger. A phosgene-mediated dealkylation of triethylamine was observed when this base was used instead of pyridine. Taking advantage of this observation, a strategy of synthesis of carbamoyl chlorides from tertiary amines and phosgene has been developed. N-Alkyl-N-benzyl(substituted)tetrahydroisoquinolines, -piperazines, -piperidines, or -anilines were treated with stoichiometric amounts of phosgene (or BTC) in CH2Cl2. Tertiary amines bearing electron-enriched benzyl group(s) afforded carbamoyl chlorides in excellent yields and without any contamination by symmetrical ureas. Subsequent additions of primary or secondary amines to these carbamoyl chlorides produced unsymmetrical ureas in single-pot and high-yielding operations. This methodology was applied in 11C-chemistry. From [ 11C]phosgene, a common precursor used in the preparation of radiotracers for positron emission tomography, a rapid and efficient synthesis of 11C-carbamoyl chlorides and 11C-unsymmetrical ureas derived from tetrahydroisoquinoline and piperazine is described. The first example of 11C-amide formation from the reaction of a 11C-carbamoyl chloride and an organometallic (cyanocuprate or a Grignard reagent in the presence of a nickel catalyst) is also presented.