Hydrochloric Acid → HCID 67391814, compound

HRID 907367Notes

Reaction equation

HRID 907367 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](/[CH:11]=[CH:12]/[C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=[O:18])=[CH:15][CH:14]=2)[CH:2]=1.O.[OH-].[Na+].Cl>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](/[CH:11]=[CH:12]/[C:13]2[CH:22]=[CH:21][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 67392595HCID 67392595, compound

Product 1

HCID 67391814HCID 67391814, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[(E)-2-(3-quinolinyl)ethenyl]benzoate (0.840 mg, 3.36 mmol; see step (i) above) was suspended in methanol (10 mL) and water (20 mL) to which sodium hydroxide solution (NaOH 0.580 g, 14.5 mmol in water 10 mL) was added with stirring. The reaction mixture was heated under reflux for 2 h. At the beginning the starting material dissolved then white precipitate appeared. The reaction mixture was cooled in an ice bath then (dilute HCl was added dropwise with vigorous stirring until pH 2 was attained. The title compound formed as a yellow solid material, which was filtered off, washed with water and dried in vacuo at 60° C. (0.640 g, 69%), m.p.=287-290° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. dissolutionAt the beginning the starting material dissolved
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. stirringwith vigorous stirring until pH 2

Sources & evidence

ORD record
ord-fe99ae1d06d347eaa2ed046f5a8806b5
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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