4-Methylquinoline → HCID 18681464, compound

HRID 1699598Notes

Reaction equation

HRID 1699598 reaction equation
CC1C=CC(S([O-])(=O)=O)=CC=1.CN1C2C(S/C/1=[CH:22]\[C:23]1[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N+:26]([CH3:33])=[CH:25][CH:24]=1)=CC=CC=2.[Br:34]C[CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40].N1C2C(=CC=CC=2)C(C)=CC=1>O1CCOCC1>[Br-:34].[C:39]([CH2:38][CH2:37][CH2:36][CH2:33][NH+:26]1[C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]([CH3:22])[CH:24]=[CH:25]1)([OH:41])=[O:40]

Participants

5

Reactant 3

HCID 102854-MethylquinolineHCID 163685-Bromovaleric acidHCID 6438345107091-89-4

Product 1

HCID 18681464HCID 18681464, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The synthesis of the carboxylic acid derivative of thiazole orange was adapted from published procedures, L. G. S. Brooker, et al., J. Am. Chem. Soc. 64:199-210 (1942); H. S. Rye, et al., Nucl. Acids Res. 20:2803-2812 (1992). 5.7 g (32 mmol) of 5-bromovaleric acid and 1.5 mL (11 mmol) of lepidine were refluxed in 30 mL of distilled dioxane under nitrogen overnight. The reaction mixture was allowed to cool to room temperature and filtered. The precipitate was washed twice with 10 mL of dioxane followed by 50 mL of petroleum ether to yield 2.6 g (70%) of pure 1-(4-Carboxybutyl)-4 -methyl-1,4-dihydro-quinolinium bromide.

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed twice with 10 mL of dioxane

Sources & evidence

ORD record
ord-7efd199e35314598b888069d4ce7cbb9
Source dataset
uspto-grants-2002_02
Patent number
US06348317B1

Reaction notes

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