Hydrogen Bromide → N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline hydrobromide

HRID 634909Notes

Reaction equation

HRID 634909 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].[BrH:18]>C(O)(=O)C>[BrH:18].[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

4

Reactant 2

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

Product 1

HCID 21260952N-ethyl-7-hydroxy-2,2,4-trimethyl-1,2-dihydroquinoline hydrobromideYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

60 g (0.25 mol) N-ethyl-2,2,4-trimethyl-7-methoxy-1,2-dihydroquinoline was dissolved in 150 ml glacial acetic acid and 150 ml hydrobromic acid was added. The solution was refluxed for 24 h. The cooled solution was stirred in an ice/methanol bath. Subsequently the precipitate was filtered and washed several times with acetone. Colourless crystals were formed in a yield of 85%.

Workup

  1. temperatureThe solution was refluxed for 24 h
  2. filtrationSubsequently the precipitate was filtered
  3. washwashed several times with acetone
  4. customColourless crystals were formed in a yield of 85%

Sources & evidence

ORD record
ord-0e6936646cc4469fb58c7b1693219c31
Source dataset
uspto-grants-2001_02
Patent number
US06184379B2

Reaction notes

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