Hydrochloric Acid → 2,7-Dimethylquinolin-6-ol

HRID 2207047Notes

Reaction equation

HRID 2207047 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.Cl.[CH:11](=O)/[CH:12]=[CH:13]/[CH3:14]>C1(C)C=CC=CC=1>[CH3:14][C:13]1[CH:12]=[CH:11][C:7]2[C:2](=[CH:3][C:4]([CH3:9])=[C:5]([OH:8])[CH:6]=2)[N:1]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 760815-Amino-2-hydroxytolueneHCID 447466Crotonaldehyde

Product 1

HCID 666314242,7-Dimethylquinolin-6-ol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To 4-amino-2-methylphenol (Aldrich, 5.0 g, 40.6 mmol) was added 6M HCl (100 mL) and heated to 100° C. with stirring. Toluene (30 mL) was added, followed with the slow addition of crotonaldehyde (6.7 mL, 81.2 mmol) at 100° C. The mixture was stirred at 100° C. for 2 additional hours, cooled to room temperature. The water layer was separated, neutralized by NaHCO3 solution. The solid formed was filtered and collected. LCMS-ESI+ (m/z): [M+H]+ calc'd for C11H12NO: 174.2; Found: 174.2.

Workup

  1. stirringThe mixture was stirred at 100° C. for 2 additional hours
  2. temperaturecooled to room temperature
  3. customThe water layer was separated
  4. customThe solid formed
  5. filtrationwas filtered
  6. customcollected

Sources & evidence

ORD record
ord-8e95fc38a08945cbb0c1f1e6908cd138
Source dataset
uspto-grants-2016_06
Patent number
US09376392B2

Reaction notes

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