Methyl iodide → Methyl 5-bromoquinoline-8-carboxylate

HRID 2281002Notes

Reaction equation

HRID 2281002 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([OH:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:15](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 592928605-Bromoquinoline-8-carboxylic acid

Product 1

HCID 71607288Methyl 5-bromoquinoline-8-carboxylateYield 14.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-Bromoquinoline-8-carboxylic acid (30 g, 0.119 mol, crude) in DMF (400 ml) was added potassium carbonate (41.12 g, 0.297 mol) and MeI (22.3 ml, 0.357 mol) at RT. The reaction mixture was stirred at RT for 12 h and the reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was filtered and evaporated. The reaction mixture was basified with 10% NaHCO3 and extracted with ethyl acetate. The organic layer was washed with water, brine and dried over sodium sulphate and concentrated to afford the title compound as brown liquid (4.6 g). LCMS: Mass found (M+, 268). 1H NMR (DMSO-d6 400 MHz): δ 9.04-9.02 (dd, J=3.92, 5.68, Hz, 1H), 8.58-8.56 (m, 1H), 8.05-8.03 (d, J=7.72 Hz, 1H), 7.87-7.86 (d, J=7.76 Hz, 1H), 7.78-7.75 (dd, J=8.6, 12.8 Hz, 1H), 3.91 (s, 3H).

Workup

  1. customAfter completion of reaction the reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7b3c245f13774157925e73d63e9fa9e5
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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