5-Bromo-6-methoxy-2-methylquinoline → 475682-40-7

HRID 859996Notes

Reaction equation

HRID 859996 reaction equation
[Br:1][C:2]1[C:11]([O:12]C)=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2>Br>[BrH:1].[Br:1][C:2]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:14])=[N:7]2

Participants

3

Reactant 1

HCID 114252565-Bromo-6-methoxy-2-methylquinoline

Product 1

HCID 86593645475682-40-7Yield 182.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 5-bromo-2-methyl-6-methoxyquinoline (30 g, 0.12 mol) in 48% HBr (135 mL) was heated to reflux for 7 hours then cooled to 5° C. in 1 hour to give a brown and thick slurry. The slurry was stirred at 0–5° C. for 1 hour then filtered, washed with EtOAc (2×50 mL) and dried in a vacuum oven to give 34.9 g (92%) of the title compound as a brown solid: 1H NMR (DMSO) δ 8.26 (d, J=8.7 Hz, 1H), 7.85 (d, J=9.1 Hz, 1H), 7.56 (d, J=9.1 Hz, 1H), 7.45 (d, J=8.7 Hz, 1H), 2.64 (s, 3H); 13C NMR (DMSO) δ 155.7, 152.0, 142.8, 133.3, 128.9, 126.4, 123.3, 121.2, 103.3, 24.1.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 hours
  3. customto give a brown and thick slurry
  4. filtrationthen filtered
  5. washwashed with EtOAc (2×50 mL)
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-14027bfabecb4648b4ba48efb6a5533b
Source dataset
uspto-grants-2006_12
Patent number
US07153849B2

Reaction notes

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