N-bromobutanimide → HCID 24962571, compound

HRID 1522832Notes

Reaction equation

HRID 1522832 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([C:13]#[N:14])[CH:12]=1)[C:9](=[O:15])[N:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)[CH:7]=[CH:6]2.[Br:24]N1C(=O)CCC1=O>>[Br:24][C:6]1[C:5]2[C:10](=[C:11]([C:13]#[N:14])[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9](=[O:15])[N:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 67184N-bromobutanimideHCID 24962570HCID 24962570, compound

Product 1

HCID 24962571HCID 24962571, compoundYield 83.3%

Procedure

Compound 6-methoxy-2-(4-methoxyphenyl)-1-oxo-1,2-dihydroisoquinoline-8-carbonitrile (0.22 g, 0.72 mmol) and N-bromosuccinimide (0.15 g, 0.86 mmol) were placed in a dry, argon flushed 150 mL single-necked flask fitted with a stirring bar and sealed with a rubber stopper. Acetonitrile (10 mL) was added via a syringe at room temperature under argon atmosphere. After the mixture was stirred at room temperature for 4 hours, the solvent was removed under reduced pressure. The residue was purified by flash column chromatography (silica-gel, hexanes/EtOAc=2/3 v/v) to give a white solid product, 0.23 g, 83.3% yield. M.p. ° C. (decomposed). MS: m/z 387.1 [M+H]+. 1H NMR (DMSO-d6, 300 MHz), δ 8.01 (s, 1H), 7.81 (d, 1H, J=2.4 Hz), 7.43 (d, 1H, J=2.4 Hz), 7.42 (d, 2H, J=8.7 Hz), 7.07 (d, 2H, J=8.7 Hz), 4.02 (s, 3H), 3.82 (s, 3H).

Workup

  1. customflushed 150 mL single-necked flask
  2. customfitted with a stirring bar
  3. customsealed with a rubber stopper
  4. additionAcetonitrile (10 mL) was added via a syringe at room temperature under argon atmosphere
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash column chromatography (silica-gel, hexanes/EtOAc=2/3 v/v)
  7. customto give a white solid product, 0.23 g, 83.3% yield

Sources & evidence

ORD record
ord-5d0e6346f9404d849a2dc04d6248a8a0
Source dataset
uspto-grants-2015_07
Patent number
US09078888B2

Reaction notes

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