2,3-Dimethylphenol → 2-(3-Chloro-2-methylphenoxy)ethyl 7-bromo-1a,2-dihydro-1H-cyclopropa[c]quinoline-3(7bH)-carboxylate

HRID 2175270Notes

Reaction equation

HRID 2175270 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12]([O:14][CH2:15][CH2:16]OC1C=CC=C(C)C=1C)=[O:13].Br[CH:27]1C2C1CNC1C=CC=CC=12.CC1C(C)=CC=CC=1O.[Cl:47][C:48]1[C:49]([CH3:55])=[C:50]([OH:54])[CH:51]=[CH:52][CH:53]=1>>[Br:1][C:2]1[C:3]2[CH:4]3[CH2:27][CH:5]3[CH2:6][N:7]([C:12]([O:14][CH2:15][CH2:16][O:54][C:50]3[CH:51]=[CH:52][CH:53]=[C:48]([Cl:47])[C:49]=3[CH3:55])=[O:13])[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 106872,3-DimethylphenolHCID 148563-Chloro-o-cresolHCID 709828952-(2,3-Dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylateHCID 86712576bromo-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Product 1

HCID 867125912-(3-Chloro-2-methylphenoxy)ethyl 7-bromo-1a,2-dihydro-1H-cyclopropa[c]quinoline-3(7bH)-carboxylate

Procedure

The title compound was prepared using a procedure analogous to 2-(2,3-dimethylphenoxy)ethyl 5-bromo-3,4-dihydroquinoline-1(2H)-carboxylate except that 5-bromo-1,2,3,4-tetrahydroquinoline, HCl salt was replaced with bromo-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline, and 2,3-dimethylphenol was replaced with 3-chloro-2-methylphenol. LCMS, [M+Na]+=460.0.

Sources & evidence

ORD record
ord-c2942e52f897424aa7c558482b179858
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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