Hydrogen Bromide → 1-Ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-ol

HRID 1483230Notes

Reaction equation

HRID 1483230 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13]C)[CH:11]=2)[C:6]([CH3:15])=[CH:5][C:4]1([CH3:17])[CH3:16])[CH3:2].Br.[OH-].[Na+]>C(O)(=O)C>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:13])[CH:11]=2)[C:6]([CH3:15])=[CH:5][C:4]1([CH3:16])[CH3:17])[CH3:2]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 154511021-Ethyl-7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 154511031-Ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-olYield 112%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound 1-ethyl-7-methoxy-2,2,4-trimethyl-1,2-dihydroquinoline (5.72 g) from Example 2 was added to a mixture of concentrated hydrobromic acid (13 mL) and glacial acetic acid (13 mL). After the mixture was stirred at reflux for 6 hours, it was cooled with ice and neutralized with 10 N aqueous sodium hydroxide to pH 7. The mixture was then extracted with chloroform (3×50 ml) and dried over anhydrous sodium sulfate, then filtered and evaporated to give a sticky green oil as the crude product (6.02 g), which was used without further purification. The structure of 1-ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-ol is given below;

Workup

  1. temperatureat reflux for 6 hours
  2. extractionThe mixture was then extracted with chloroform (3×50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ad239d050cf5443781e1c1d299442c0d
Source dataset
uspto-grants-2016_08
Patent number
US09416153B2

Reaction notes

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