3,4-Dichlorobenzaldehyde → 6-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023199Notes

Reaction equation

HRID 1023199 reaction equation
[N+:1]([N:3]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[C-:2].[Cl:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH:27]=[O:28].[O:33]=[C:34]1[CH2:43][CH2:42][C:41]2[C:36](=[CH:37][CH:38]=[C:39]([O:44][CH2:45][C:46]([OH:48])=O)[CH:40]=2)[NH:35]1>ClCCl>[Cl:23][C:24]1[CH:25]=[C:26]([CH:27]([OH:28])[C:2]2[O:48][C:46]([CH2:45][O:44][C:39]3[CH:40]=[C:41]4[C:36](=[CH:37][CH:38]=3)[NH:35][C:34](=[O:33])[CH2:43][CH2:42]4)=[N:3][N:1]=2)[CH:29]=[CH:30][C:31]=1[Cl:32]

Participants

5

Reactant 3

HCID 227103,4-DichlorobenzaldehydeHCID 11266621(Isocyanoimino)triphenylphosphoraneHCID 128192822-[(2-Oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy]acetic acid

Product 1

HCID 894669846-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-oneYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-isocyaniminotriphenylphosphorane (0.204 g, 0.678 mmol), 3,4-dichlorobenzaldhyde (0.158 g, 2.712 mmol), and 2-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)acetic acid (0.150 g, 0.678 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight. Solvent was removed under vacuum. The crude product was recystallised in ACN/Ethanol to afford 6-((5-((3,4-dichlorophenyl)(hydroxy)methyl)-1,3,4-oxadiazol-2-yl)methoxy)-3,4-dihydroquinolin-2(1H)-one (40 mg, 14%) as an off white solid. 1H NMR: 400 MHZ, DMSO-d6: δ 2.40 (t, J=7.20 Hz, 2H), 2.82 (t, J=8.00 Hz, 2H), 5.32 (s, 2H), 6.11 (d, J=5.60 Hz, 1H), 6.77 (d, J=8.40 Hz, 1H), 6.82 (dd, J=2.40, 8.60 Hz, 1H), 6.88 (s, 1H), 7.00 (d, J=5.60 Hz, 1H), 7.45 (dd, J=1.60, 8.40 Hz, 1H), 7.67 (d, J=8.40 Hz, 1H), 7.72 (d, J=1.60 Hz, 1H), 9.95 (s, 1H). LCMS: RT 1.76 min. LCMS (ES-API), m/z 422.0 (M+H).

Workup

  1. customSolvent was removed under vacuum

Sources & evidence

ORD record
ord-2d7908c06ea04da395e312500164a744
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

Loading…