Hydrochloric Acid → 2-Methylquinolin-5-ol

HRID 2424402Notes

Reaction equation

HRID 2424402 reaction equation
[NH2:1][C:2]1[C:3](Br)=[CH:4][C:5](Br)=[C:6]([OH:8])[CH:7]=1.Cl.[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].NC1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:15][C:14]1[CH:13]=[CH:12][C:7]2[C:6]([OH:8])=[CH:5][CH:4]=[CH:3][C:2]=2[N:1]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 447466CrotonaldehydeHCID 516892Sodium BicarbonateHCID 114825265-Amino-2,4-dibromophenol

Product 1

HCID 1354402792-Methylquinolin-5-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred mixture of the 5-amino-2,4-dibromophenol prepared in example 3 (13 g, 49 mmol), acetic acid (65 mL) and HCl (65 mL) was added crotonaldehyde and the resultant mixture was heated at reflux for 1.5 h under argon. HBr (65 mL) and aniline (13 mL) were added and the mixture was refluxed for 5 h. After cooling, the reaction mixture was neutralized by adding of NaHCO3 (˜180 g) and then extracted with EtOAc. The organic extract was dried (MgSO4) and concentrated in vacuo to give a black solid (22 g). The crude product was purified by column chromatography (eluents: CH2Cl2-MeOH 98:2). Yield 5 g (49%) brown-white solid. Rf=0.43 (CH2Cl2-MeOH 9:1).

Workup

  1. temperatureat reflux for 1.5 h under argon. HBr (65 mL)
  2. temperaturethe mixture was refluxed for 5 h
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-94895107577046a6a85d3fe52f72e1d4
Source dataset
uspto-grants-2011_06
Patent number
US07964603B2

Reaction notes

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