Benzoyl Peroxide → HCID 117727907, compound

HRID 1772681Notes

Reaction equation

HRID 1772681 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:42][CH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 1074072ethyl 2-methylquinoline-4-carboxylate

Product 1

HCID 117727907HCID 117727907, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a refluxing solution of ethyl 2-methylquinoline-4-carboxylate (1.6 g, 7.60 mmol) in CCl4 (150 mL), benzoyl peroxide (186 mg, 0.767 mmol) was added followed by NBS (750 g, 4.23 mmol). After 1 h, a second batch of NBS (750 g, 4.23 mmol) was added and the refluxing was continued overnight. The reaction mixture was allowed to cool to rt and washed with satd. Na2CO3. The organic layer was separated, dried (Na2SO4) and concentrated. The residue obtained was purified by flash column chromatography on silica gel (0:100-2:3 EtOAc/heptanes) to obtain ethyl 2-(bromomethyl)quinoline-4-carboxylate. Mass Spectrum (LCMS, ESI pos.) Calcd. For C13H12BrNO2: 294.0 (M+H). Found 294.1.

Workup

  1. waitthe refluxing was continued overnight
  2. washwashed with satd
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customwas purified by flash column chromatography on silica gel (0:100-2:3 EtOAc/heptanes)

Sources & evidence

ORD record
ord-a55eabd800994591ad4ed961dcf14b64
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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