N-bromobutanimide → N-(7-(bromomethyl)quinolin-2-yl)acetamide

HRID 1503145Notes

Reaction equation

HRID 1503145 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([CH3:15])=[CH:10][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][C:9]([CH2:15][Br:16])=[CH:10][CH:11]=2)[N:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 11159961N-(7-methylquinolin-2-yl)acetamide

Product 1

HCID 11311996N-(7-(bromomethyl)quinolin-2-yl)acetamideYield 64.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

Compound 20 (0.265 g, 1.32 mmol) was diluted in anhydrous benzene (10 mL). N-Bromosuccinimide (0.247 g, 1.39 mmol) and a catalytic amount (0.020 g) of benzoyl peroxide were added, and the mixture was heated to reflux under argon until an orange tint was no longer visible in the solution refluxing in the condenser (typically 4 h). The mixture was cooled, concentrated, and purified by flash column chromatography (SiO2), eluting with a gradient of 7% to 14% EtOAc in CH2Cl2, to yield the product (0.236 g, 64%) as a flocculent yellow solid. 1H NMR chemical shifts for this compound are consistent with those reported in the literature for the 7-isomer. 1H-NMR (500 MHz; CDCl3): δ 8.43-8.41 (m, 2 H), 8.16 (d, J=8.9 Hz, 1 H), 7.79-7.77 (m, 2 H), 7.49 (dd, J=8.4, 1.7 Hz, 1 H), 4.65 (s, 2 H), 2.27 (s, 3 H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under argon until an orange tint
  3. temperaturerefluxing in the condenser (typically 4 h)
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (SiO2)
  7. washeluting with a gradient of 7% to 14% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-a1b2e95afbf9477eba90f6197707ba71
Source dataset
uspto-grants-2015_12
Patent number
US09212144B2

Reaction notes

Loading…