N-bromobutanimide → HCID 24962933, compound

HRID 1522826Notes

Reaction equation

HRID 1522826 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH:7]=[CH:6]2.[Br:22]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:22][C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9](=[O:13])[N:8]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimide2×HCID 516892Sodium BicarbonateHCID 57557417HCID 57557417, compound

Product 1

HCID 24962933HCID 24962933, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Methoxy-2-(4-methoxyphenyl)isoquinolin-1(2H)-one (0.50 g, 1.78 mmol) was placed in a dry 250 mL single-necked round-bottomed flask fitted with a stirring bar and septa. Acetonitrile (10 mL) was added via a syringe under argon atmosphere at room temperature. N-Bromosuccinimide or NBS (0.33 g, 1.87 mmol) was added portionwise under argon atmosphere at room temperature. The reaction mixture was allowed to stir at room temperature for 2 hours. 20 mL of saturated sodium bicarbonate solution was then added. The mixture was extracted with ethyl acetate (3×10 mL). Organic layers were separated, dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by flash column chromatography (silica gel, hexanes/EtOAc=2/3 v/v) to give a white solid product, 0.55 g, 85.9% yield. MS: 360.4 [M+H]+. 1H NMR (DMSO-d6, 300 MHz): δ 8.14 (d, 1H, J=8.7 Hz), 7.39-7.34 (m, 3H), 7.19 (d, 1H, J=2.4 Hz), 7.13-7.03 (m, 3H), 6.62 (dd, 1H, J=7.5 Hz), 3.89 (s, 3H), 3.81 (s, 3H).

Workup

  1. customfitted with a stirring bar
  2. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  3. customOrganic layers were separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash column chromatography (silica gel, hexanes/EtOAc=2/3 v/v)
  7. customto give a white solid product, 0.55 g, 85.9% yield

Sources & evidence

ORD record
ord-3bbbf633bdf04ae185e18d453f8ea44f
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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