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Allyl bromide → HCID 58026901, compound

HRID 1966291
Notes
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Reaction equation

HRID 1966291 reaction equation
[C:1]([O:5][CH2:6][C:7]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([CH3:27])=[CH:10][C:11]([CH3:26])([CH3:25])[NH:12]2)(=[O:4])[CH:2]=[CH2:3].[CH2:28](Br)[CH:29]=[CH2:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][CH2:6][C:7]1[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9]([CH3:27])=[CH:10][C:11]([CH3:26])([CH3:25])[N:12]2[CH2:30][CH:29]=[CH2:28])(=[O:4])[CH:2]=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 580268935-Acryloyloxymethyl-6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Product 1

HCID 58026901HCID 58026901, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-acryloyloxymethyl-6-(2-methoxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Compound No. 1-7, 50 mg, 0.14 mmol), allylbromide (111 μL, 1.28 mmol) and potassium carbonate (78 mg, 0.56 mmol) was suspended in anhydrous N,N-dimethylformamide (2 mL), and the reaction mixture was stirred at 60° C. for 4 days. After cooling down, it was diluted with ethyl acetate (25 mL). The whole was washed with water (30 mL, twice) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (23 mg) as a pale yellow oil. (Yield 41%)

Workup

  1. temperatureAfter cooling down
  2. washThe whole was washed with water (30 mL
  3. dry with materialtwice) and saturated brine (30 mL) successively, dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-143f10f5964f459d90a6b8bc01b61524
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420635B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes