8-Hydroxyquinoline-5-carbaldehyde → HCID 135744156, compound

HRID 2213700Notes

Reaction equation

HRID 2213700 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14].[CH:15]([C:17]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2)=O>C1C=CC=CC=1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]=[CH:15][C:17]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[N:22]2

Participants

4

Reactant 2

HCID 2753638-Hydroxyquinoline-5-carbaldehydeHCID 21958336HCID 21958336, compound

Product 1

HCID 135744156HCID 135744156, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Amine 4 (0.726 g, 0.00376 mol) and 5-formyl-8-hydroxyquinoline 6 (0.650 g, 0.00376 mol) were dissolved in 40 mL of benzene and refluxed for 18 hours. After cooling, the solvent was removed under reduced pressure to yield the product as an orange solid (1.308 g, 100%). 1H NMR (300 MHz, CDCl3) δ9.75 (1H, dd J=8.79, 1.64); 8.81 (1H, dd, J=1.64, 4.39); 8.59 (1H, s); 7.69 (1H, d, J=8.24); 7.56 (1H, dd, J=4.39, 8.79); 7.19 (1H, d, J=7.69); 6.10 (1H endo, dd, J=2.74, 5.49); 6.06–5.99 (2H exo, m); 5.91 (1H endo, dd, J=2.74, 5.94); 3.67 (2H, t, J=7.14); 2.74 (2H, s); 1.99–1.69 (4H, m); 1.42–1.01 (12H, m); 0.50–0.44 (1H, m). 13C NMR (75 MHz, CDCl3) δ160.8; 154.2; 148.1; 138.4; 137.0; 135.3; 133.0; 132.6; 127.0; 123.3; 123.2; 109.2; 62.9; 49.7; 45.6; 42.7; 38.9; 34.9; 32.6; 31.4; 29.9; 28.8; 27.6. HRMS (EI): calcd for C23H28N2O1 [M]+348.2201, found 348.2186.

Workup

  1. temperaturerefluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a7878156fac0466faa0b57dd60b21d6f
Source dataset
uspto-grants-2006_09
Patent number
US07105617B2

Reaction notes

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