Acetone → 5-Bromoquinoline-8-carboxaldehyde

HRID 2281000Notes

Reaction equation

HRID 2281000 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12](Br)Br)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.CC(C)=[O:17]>O.[N+]([O-])([O-])=O.[Ag+]>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[O:17])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 2

HCID 180AcetoneHCID 672475935-Bromo-8-(dibromomethyl)quinoline

Product 1

HCID 164142435-Bromoquinoline-8-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

To a solution of 5-Bromo-8-(dibromomethyl)quinoline (75 g, 0.197 mol) in Acetone (400 ml), Water (100 ml) was added Silvernitrate (75 g) at 0° C. in lots for 10 min and this reaction mixture was stirred at RT for 6 h. The reaction completion was confirmed by TLC. After completion of reaction the reaction mixture was filtered and the filterate was extracted with MTBE (1000 ml). The organic layer was washed with 10% NaHCO3 solution water, brine and the organic layer was dried over sodium sulphate and concentrated to afford the title compound as off white solid (15 g, 32% yield). 1H NMR (DMSO-d6 400 MHz): δ 11.272-11.27 (s, 1H), 9.17-9.15 (dd, J=4.2, 5.8 Hz, 1H), 8.64-8.62 (dd, J=8.6, 10.3 Hz, 1H), 8.17-8.15 (d, J=7.84, 1H), 8.09-8.07 (d, J=7.88 Hz, 1H), 7.85-7.82 (dd, J=8.64, 12.84 Hz, 1H).

Workup

  1. customAfter completion of reaction the reaction mixture
  2. filtrationwas filtered
  3. extractionthe filterate was extracted with MTBE (1000 ml)
  4. washThe organic layer was washed with 10% NaHCO3 solution water, brine
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-160a74b3f865495fa218b5300f6c95b0
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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