681827-50-9

Basic information

• Product Name: 1(2H)-Quinolinecarboxylic acid, 3,4-dihydro-2-methyl-4-oxo-, phenylmethyl ester
• CAS NO: 681827-50-9
• Molecular Formula: C18H17NO3
• Molecular Weight: 295.338
• Mol File: 681827-50-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1(2H)-Quinolinecarboxylic acid, 3,4-dihydro-2-methyl-4-oxo-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Quinolinecarboxylic acid, 3,4-dihydro-2-methyl-4-oxo-, phenylmethyl ester(681827-50-9)
• EPA Substance Registry System: 1(2H)-Quinolinecarboxylic acid, 3,4-dihydro-2-methyl-4-oxo-, phenylmethyl ester(681827-50-9)

Safety Data

• Hazardous Substances Data: 681827-50-9(Hazardous Substances Data)

Upstream product

• 577-59-3 2-acetylnitrobenzene 
• 529-37-3 4(1H)-quinolinone 
• 87488-61-7 3-(dimethylamino)-1-(2-nitrophenyl)prop-2-en-1-one 
• 75-16-1 methylmagnesium bromide 
• 172538-83-9 benzyl 4-oxoquinoline-1(4H)-carboxylate 
• 611-35-8 4-chloroquinoline 
• 607-31-8 4-methoxyquinoline 
• 676-58-4 methylmagnesium chloride 
• 501-53-1 benzyl chloroformate 
• 611-36-9 quinolin-4-ol 

Downstream Products

• 681827-56-5 2-methyl-4-benzylimino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester 
• 681827-51-0 2-methyl-4-phenylimino-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester 
• 1057220-80-0 benzyl 4-(cyclopropylamino)-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate 

Relevant articles and documents

Conjugate Addition Routes to 2-Alkyl-2,3-dihydroquinolin-4(1H)-ones and 2-Alkyl-4-hydroxy-1,2-dihydroquinoline-3-carboxylates

Under CuBr·SMe2/PPh3 catalysis (5/10 mol-%) RMgCl (R = Me, Et, nPr, CH=CH2, nBu, iBu, nC5H11, cC6H11, Bn, CH2Bn, nC11H23) readily (–78 °C) undergo 1,4-addition to Cbz or Boc protected quinolin-4(1H)-ones to provide 2-alkyl-2,3-dihydroquinolin-4(1H)-ones (14 examples, 54–99 % yield). Asymmetric versions require AlEt3 to Boc-protected ethyl 6-substituted 4(1H)-quinolone-3-carboxylates (6-R group = all halogens, n/i/t-alkyls, CF3) and provide 61–91 % yield, 30–86 % ee; any halogen, Me, or CF3 provide the highest stereoselectivities (76–86 % ee). Additions of AlMe3 or Al(nC8H17)3 provide ≈ 45 and ≈ 75 % ee on addition to the parent (6-R = H). Ligand (S)-(BINOL)P–N(CHPh2)(cC6H11) provides the highest ee values engendering addition to the Si face of the 4(1H)-quinolone-3-carboxylate. Allylation and deprotection of a representative 1,4-addition product example confirm the facial selectivity (X-ray crystallography).

Tetrahydroquinoline derivatives as CRTH2 antagonists

The invention relates to compounds of formula (I) wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the description, their use as medicament, pharmaceutical compositions containing them and processes for their preparation.