Chloroacetaldehyde → Hydrochloric Acid

HRID 461002Notes

Reaction equation

HRID 461002 reaction equation
[Cl:1][CH2:2][CH:3]=O.[NH2:5][C:6]1[C:15]([CH3:17])([CH3:16])[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=1.C(=O)(O)[O-].[Na+]>C(O)C.O.C1(C)C(C)=CC=CC=1>[CH3:16][C:15]1([CH3:17])[C:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([OH:18])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]2[CH:2]=[CH:3][N:5]=[C:6]12.[ClH:1]

Participants

8

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 21395181HCID 21395181, compound

Product 2

HCID 313Hydrochloric AcidYield 263.3%HCID 21395174HCID 21395174, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

To a solution of freshly prepared chloroacetaldehyde (2.30 g., 0.03 mole) in absolute ethanol (50 ml.) and water (12.5 ml.) was added a solution of 2-amino-3,4-dihydro-3,3-dimethyl-4-phenylquinolin-4-ol (6.66 g., 0.025 mole) in absolute alcohol (62.5 ml). Sodium bicarbonate (2.5 g) was added and the mixture refluxed for 6 hours. After cooling, a small precipitate was filtered off, and the filtrate concentrated in vacuo, taken up in water, extracted with ether, dried and evaporated. The residue was crystallised from isopropyl alcohol to give an intermediate (3.77 g., m.p. 188°-190° C). A solution of this intermediate in dried xylene (200 ml.) was refluxed under a Dean and Stark head for 21 hours, cooled and the xylene evaporated. The hydrochloride of the residue was recrystallised from isopropyl alcohol to give the title compound as its hydrochloride (2.4 g., 258°-260° C).

Workup

  1. temperaturethe mixture refluxed for 6 hours
  2. temperatureAfter cooling
  3. filtrationa small precipitate was filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. extractionextracted with ether
  6. customdried
  7. customevaporated
  8. customThe residue was crystallised from isopropyl alcohol
  9. customto give an intermediate (3.77 g., m.p. 188°-190° C)
  10. temperaturecooled
  11. customthe xylene evaporated
  12. customThe hydrochloride of the residue was recrystallised from isopropyl alcohol

Sources & evidence

ORD record
ord-b217fb8374724ca38014cadf53d548f0
Source dataset
uspto-grants-1977_12
Patent number
US04061754

Reaction notes

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