3,4-Dichlorobenzyl chloride → 2-(3,4-Dichlorobenzyl)-1,2-dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

HRID 894391Notes

Reaction equation

HRID 894391 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][C:6](=[O:18])[C:7]2[C:12]([C:13]=1[CH2:14][C:15]([OH:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=2.[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23]Cl>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[Cl:28])[CH2:23][N:5]1[C:4]([CH3:3])=[C:13]([CH2:14][C:15]([OH:17])=[O:16])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:18]

Participants

5

Reactant 3

HCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 127155091,2-Dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

Product 1

HCID 127155122-(3,4-Dichlorobenzyl)-1,2-dihydro-3-methyl-1-oxo-4-isoquinoline Acetic Acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (48 mg., 2.0 mmol) (Ventron, washed free of mineral oil with hexane) and 2 ml. dimethylformamide were reacted with 1,2-dihydro-3-methyl-1-oxo-4-isoquinoline acetic acid (217 mg., 1.0 mmol). After homogeneity was observed, 3,4-dichlorobenzyl chloride (196 mg., 1.0 mmol) in 1 ml. dimethylformamide was added. The mixture was heated at 110° for 3 hr, cooled and partitioned between hydrochloric acid and ethyl acetate. The crude product obtained from the organic layer after several aqueous washings, drying over magnesium sulfate, filtration, and vacuum evaporation was column chromatographed on silica gel with ethyl acetate; 104 mg., 28%, mp 218°-220°.

Workup

  1. temperatureThe mixture was heated at 110° for 3 hr
  2. temperaturecooled
  3. custompartitioned between hydrochloric acid and ethyl acetate

Sources & evidence

ORD record
ord-20d21f62612741e2a9455abbb68e36e2
Source dataset
uspto-grants-1981_08
Patent number
US04283539

Reaction notes

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