HCID 10091372, compound → 2-methyl-3H-quinolin-4-one

HRID 1757278Notes

Reaction equation

HRID 1757278 reaction equation
Cl.[CH3:2][C:3]1[CH:12]=[C:11]([O:13]CC2C=CC(C3C(C(O)=O)=CC=CC=3)=CC=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.CS(C)=O.[N+](C1C=C(C=CC=1)CO)([O-])=O.CC1C=C(OCC2C=CC(C3C(C(OC)=O)=CC=CC=3)=CC=2)C2C(=CC=CC=2)N=1>>[CH3:2][C:3]1[CH2:12][C:11](=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1

Participants

4

Reactant 3

HCID 10091372HCID 10091372, compoundHCID 10453971HCID 10453971, compoundHCID 86748928HCID 86748928, compound

Product 1

HCID 27850602-methyl-3H-quinolin-4-one

Procedure

(Example 2): 4'-[(2-Methylquinolin-4-yloxy)methyl]biphenyl-2-carboxylic acid hydrochloride, m.p. 184°-186° C.; NMR (d6 -DMSO): 2.93(s,3H), 5.67(s,2H), 7.38-7.72(m,8H), 7.77(dd,1H), 7.84(dd,1H), 8.08(dt,1H), 8.29(d,1H), 8.33(d,1H); mass spectrum (-ve FAB, DMSO/m-nitrobenzyl alcohol)(NBA): 368 (M-H)- ; microanalysis found: C,71.2; H,5.0; N,3.6; Cl, 8.6%, C24H19NO3.HCl requires:C,71.0; H,5.0; N,3.5; Cl,8.7%; starting from methyl 4'-[(2-methylquinolin-4-yloxy)methyl]biphenyl-2-carboxylate, obtained as a solid, m p 146° C.; NMR: 2.71(s,3H), 3.67(s,3H), 5.33(s,2H), 6.74(s,1H), 7.3-7.6(complex m,8H), 7.68(dt,1H), 7.87(dd,1H), 7.98(d,1H), 8.23(dd,1H); itself obtained from 2-methyl-4-quinolone, using analogous procedures to those described in Example 1;

Workup

  1. customobtained as a solid, m p 146° C.

Sources & evidence

ORD record
ord-87f3320ea94e4a8aa198c1713f4abe74
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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