1-(1-Benzoyloxy-1-methylethyl)-isoquinoline → 1-(Propan-2-yl)isoquinoline

HRID 1156908Notes

Reaction equation

HRID 1156908 reaction equation
C(O[C:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1)([CH3:12])[CH3:11])(=O)C1C=CC=CC=1.[H][H]>C(O)C.[C].[Pd]>[CH:10]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 28251561-(1-Benzoyloxy-1-methylethyl)-isoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 126825361-(Propan-2-yl)isoquinolineYield 68.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

(a-2-2) Ten grams of 1-(1-benzoyloxy-1-methylethyl)-isoquinoline was dissolved in 100 ml of ethanol, and 2 g of 10% palladium-carbon was dissolved. The mixture was stirred in a stream of hydrogen at room temperature and atmospheric pressure for 24 hours. The reaction mixture was filtered through Celite, and the solvent was distilled off. Distillation under reduced pressure afforded 4.0 g of 1-isopropylisoquinoline. (b) A mixture of 9.4 g of 1-isopropylisoquinoline and 12 g of N-hydroxymethyl dichloroacetamide was dissolved in 94 g of conc. sulfuric acid and 9.5 g of 20% fuming sulfuric acid, and the solution was heated for 3 hours. The reaction mixture was poured into water, made weakly alkaline with an aqueous solution of sodium hydroxide, and extracted with ethyl acetate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate-benzene to afford 20 g of 1-isopropyl-5-dichloroacetylaminomethylisoquinoline having a melting point of 150.7° to 151.0° C.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. distillationthe solvent was distilled off
  3. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-1784e27234ec449abef036ccf6fc2d8a
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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