Water → HCID 69417696, compound

HRID 1292708Notes

Reaction equation

HRID 1292708 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:12]([OH:17])(=[O:16])/[CH:13]=[CH:14]/[CH3:15].O.[OH-].[Na+]>C1(C)C=CC=CC=1>[N:7]1[C:8]2[C:3](=[C:2]([NH:1][CH:14]([CH3:15])[CH2:13][C:12]([OH:17])=[O:16])[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 119115-AminoquinolineHCID 14798Sodium HydroxideHCID 637090Crotonic Acid

Product 1

HCID 69417696HCID 69417696, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-aminoquinoline (9.9 g, 0.069 mol) and crotonic acid (8.9 g, 0.103 mol) in toluene (35 ml) was stirred at reflux for 48 h. The reaction mixture was allowed to cool to ambient, added to water (500 ml) and the pH adjusted to 9 to 10 by the addition of 2N sodium hydroxide. The reaction mixture was screened and the filtrate extracted with diethyl ether (3×100 ml). The pH of the aqueous layer was first adjusted to pH2 with concentrated HCl and then to pH7 with calcium hydroxide. The precipitate which formed was collected by filtration, washed first with water (200 ml) and then with acetone (200 ml) before being dried to give 8.1 g of a cream solid.

Workup

  1. temperatureat reflux for 48 h
  2. temperatureto cool to ambient,
  3. extractionthe filtrate extracted with diethyl ether (3×100 ml)
  4. customThe precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed first with water (200 ml)
  7. dry with materialwith acetone (200 ml) before being dried

Sources & evidence

ORD record
ord-e796985f790a46e48b1f769398221cab
Source dataset
uspto-grants-2007_07
Patent number
US07238228B2

Reaction notes

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