2,4,5-Trichlorophenol → (5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-((3-chloro-2-methylphenoxy)methyl)cyclopropyl)methanone

HRID 2175299Notes

Reaction equation

HRID 2175299 reaction equation
ClC1C=C(Cl)C(Cl)=CC=1OCCCC(N1C2C(=C(C3C=NN(CC(OCC)=O)C=3)C=CC=2)CCC1)=O.OCCCC(N1C2C(=C(C3C=NN(CC(OCC)=O)C=3)C=CC=2)CCC1)=O.[Br:64][C:65]1[CH:74]=[CH:73][CH:72]=[C:71]2[C:66]=1[CH2:67][CH2:68][CH2:69][N:70]2[C:75]([C:77]1([CH2:80][OH:81])[CH2:79][CH2:78]1)=[O:76].ClC1C=C(Cl)C(Cl)=CC=1O.[Cl:92][C:93]1[C:94]([CH3:100])=[C:95](O)[CH:96]=[CH:97][CH:98]=1>>[Br:64][C:65]1[CH:74]=[CH:73][CH:72]=[C:71]2[C:66]=1[CH2:67][CH2:68][CH2:69][N:70]2[C:75]([C:77]1([CH2:80][O:81][C:95]2[CH:96]=[CH:97][CH:98]=[C:93]([Cl:92])[C:94]=2[CH3:100])[CH2:78][CH2:79]1)=[O:76]

Participants

6

Reactant 5

HCID 72712,4,5-TrichlorophenolHCID 148563-Chloro-o-cresolHCID 70982627Ethyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetateHCID 70983434Ethyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetateHCID 86712601(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-(hydroxymethyl)cyclopropyl)methanone

Product 1

HCID 86712602(5-Bromo-3,4-dihydroquinolin-1(2H)-yl)(1-((3-chloro-2-methylphenoxy)methyl)cyclopropyl)methanone

Procedure

The title compound was prepared using a procedure analogous to ethyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate except that ethyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate was replaced with (5-bromo-3,4-dihydroquinolin-1(2H)-yl)(1-(hydroxymethyl)cyclopropyl)methanone and 2,4,5-trichlorophenol was replaced with 3-chloro-2-methylphenol. LCMS, [M+H]+=436.1. 1H NMR (400 MHz, CDCl3) δ 7.54 (d, J=8.2 Hz, 1H), 7.33 (d, J=7.9 Hz, 1H), 7.04-6.90 (m, 3H), 6.49 (d, J=7.8 Hz, 1H), 3.92-3.82 (m, 4H), 2.65 (t, J=6.9 Hz, 2H), 2.26 (s, 3H), 1.96-1.87 (m, 2H), 1.21 (dd, J=6.9, 4.9 Hz, 2H), 0.94 (q, J=5.0 Hz, 2H).

Sources & evidence

ORD record
ord-53b644ac9de843bbadf8506adb7ccf13
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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