Acrylic Acid → HCID 232155, compound

HRID 550880Notes

Reaction equation

HRID 550880 reaction equation
Br.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.[C:15]([OH:19])(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH:14][CH2:17][CH2:16][C:15]([OH:19])=[O:18])[CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 162138508-Amino-6-methoxyquinoline hydrobromide&

Product 1

HCID 232155HCID 232155, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 5.0 g (19.56 mmol) of 6-methoxy-8-aminoquinoline hydrobromide, 1.48 ml (21.51 mmol) of acrylic acid and 5.45 ml (39.12 mmol) of triethylamine is dissolved in 25 ml of toluene and brought to 110° C. for 16 h, with magnetic stirring. 10 ml of a 10% (w/v) aqueous sodium hydroxide solution are then added and the reaction medium is kept at 100° C. for 20 min, with stirring. After returning to ambient temperature, the phase containing the toluene is eliminated and the aqueous phase is extracted with 100 ml of chloroform. The aqueous phase is then acidified by adding acetic acid until a pH of 5-6 is obtained. The precipitate obtained is filtered off and then washed with water. After drying under vacuum, the compound 26 is obtained in the form of a green powder: 1.77 g (yield=37%).

Workup

  1. waitthe reaction medium is kept at 100° C. for 20 min
  2. customAfter returning to ambient temperature
  3. extractionthe aqueous phase is extracted with 100 ml of chloroform
  4. additionby adding acetic acid until a pH of 5-6
  5. customis obtained
  6. customThe precipitate obtained
  7. filtrationis filtered off
  8. washwashed with water
  9. customAfter drying under vacuum

Sources & evidence

ORD record
ord-4c704b6edd584ede81c1ad61f64d15ef
Source dataset
uspto-grants-2011_05
Patent number
US07947701B2

Reaction notes

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