Hydrochloric Acid → HCID 136065589, compound

HRID 1924404Notes

Reaction equation

HRID 1924404 reaction equation
[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH2:13]=[O:14]>>[OH:14][CH2:13][C:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]([OH:11])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 135441757Quinolin-5-ol

Product 1

HCID 136065589HCID 136065589, compound

Procedure

3.40 g of quinolin-5-ol is combined with 8 ml of conc. hydrochloric acid and 8 ml of 37% formalin solution while cooling with an ice bath. Then hydrogen chloride gas is piped through the reaction mixture for about two hours, while the temperature slowly rises. The reaction mixture is stirred first overnight while cooling with an ice bath, then at ambient temperature and then evaporated down in vacuo. The flask residue is taken up in water, covered with a layer of diethyl ether and adjusted to pH 10 while cooling with an ice bath and vigorously stirring with dilute ammonia solution. After another two hours' vigorous stirring at ambient temperature the organic phase is separated off and the aqueous phase is extracted with diethyl ether. The combined organic phases are washed with water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with methylene chloride/methanol (20:1) as eluant.

Workup

  1. temperaturewhile cooling with an ice bath
  2. temperaturewhile cooling with an ice bath
  3. customat ambient temperature and then evaporated down in vacuo
  4. temperaturewhile cooling with an ice bath
  5. stirringvigorously stirring with dilute ammonia solution
  6. stirringAfter another two hours' vigorous stirring at ambient temperature the organic phase
  7. customis separated off
  8. extractionthe aqueous phase is extracted with diethyl ether
  9. washThe combined organic phases are washed with water and saturated sodium chloride solution
  10. dry with materialdried over magnesium sulphate
  11. customevaporated down
  12. customThe flask residue is chromatographed through a silica gel column with methylene chloride/methanol (20:1) as eluant

Sources & evidence

ORD record
ord-4501d30f343a4e67a94cb5006eb01417
Source dataset
uspto-grants-2012_05
Patent number
US08178541B2

Reaction notes

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