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

HRID 634910Notes

Reaction equation

HRID 634910 reaction equation
Br.[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[C:7]([CH3:15])=[CH:6][C:5]1([CH3:17])[CH3:16])[CH3:3].C([O-])(=O)C.[Na+].Br>O.C(Cl)(Cl)Cl>[CH2:2]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[C:7]([CH3:15])=[CH:6][C:5]1([CH3:16])[CH3:17])[CH3:3]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 517045Sodium AcetateHCID 21260952N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline hydrobromide

Product 1

HCID 154511031-Ethyl-2,2,4-trimethyl-1,2-dihydroquinolin-7-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

200 g N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline hydrobromide was suspended in a mixture of 1 l water and 500 ml chloroform. 20% sodium acetate solution was added to this suspension until the pH value reached ca. 5. The organic phase was washed with water, dried over sodium sulfate and evaporated to dryness in a rotary evaporator. A light-brown oil was obtained in this manner. Since the released base decomposes very rapidly, only the required amount of base for the further process was released from the hydrobromide.

Workup

  1. washThe organic phase was washed with water
  2. dry with materialdried over sodium sulfate
  3. customevaporated to dryness in a rotary evaporator
  4. customA light-brown oil was obtained in this manner

Sources & evidence

ORD record
ord-20f5b970b52d4e76a10484ba45fb3ed4
Source dataset
uspto-grants-2001_02
Patent number
US06184379B2

Reaction notes

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