N-bromobutanimide → N-(6-(bromomethyl)quinolin-2-yl)acetamide

HRID 1503154Notes

Reaction equation

HRID 1503154 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:15])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:15][Br:16])[CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11458305N-(6-methylquinolin-2-yl)acetamide

Product 1

HCID 11300436N-(6-(bromomethyl)quinolin-2-yl)acetamideYield 63%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

Compound 45 (0.300 g, 1.50 mmol) was diluted in anhydrous benzene (10 mL). N-Bromosuccinimide (0.280 g, 1.57 mmol) and a catalytic amount (˜0.020 g) of benzoyl peroxide were added, and the mixture was heated to reflux under nitrogen until an orange tint was no longer visible in the solution refluxing in the condenser (around 2 h 40 min). The mixture was cooled, concentrated, and purified by flash column chromatography (SiO2), eluting with a gradient of 10% to 12% EtOAc in CH2Cl2 to yield the product (0.262 g, 63%) as a flocculent yellow solid. The 1H NMR chemical shifts for this compound are identical to those previously reported in the literature. 1H-NMR (500 MHz; CDCl3): δ 8.44 (br d, J=8.6 Hz, 1 H), 8.30 (br s, 1 H), 8.17 (d, J=9.0 Hz, 1 H), 7.82 (m, J=9.1 Hz, 2 H), 7.72 (dd, J=8.6, 2.1 Hz, 1 H), 4.67 (s, 2 H), 2.29 (s, 3 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under nitrogen until an orange tint
  3. temperaturerefluxing in the condenser (around 2 h 40 min)
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (SiO2)
  7. washeluting with a gradient of 10% to 12% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-dff293a5e612415591e5165a5d333534
Source dataset
uspto-grants-2015_12
Patent number
US09212144B2

Reaction notes

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