N-(2-phenylethyl)acetamide → 1-Methyl-3,4-dihydroisoquinoline

HRID 2293123Notes

Reaction equation

HRID 2293123 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.N>CO.ClCCl>[CH3:11][C:10]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH2:7][CH2:8][N:9]=1

Participants

4

Reactant 2

HCID 70143N-(2-phenylethyl)acetamideHCID 12896473Azane;hydrate

Product 1

HCID 2315021-Methyl-3,4-dihydroisoquinolineYield 86.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

8.43 g of the compound(51.6 mM) prepared in Step 1 above was added to 84.36 g of polyphosporic acid, which was reacted at 160° C. for 1.5 hours with stirring. The reaction solution was poured into ice water, neutralized with ammonia water, and extracted from ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under a reduced pressure. The residue thus obtained was subjected to silica gel column chromatography using a mixed solvent of methanol:dichloromethane (1:20 (v/v)) as a developing solvent to give 6.48 g of the title compound as oily substance.

Workup

  1. customwas reacted at 160° C. for 1.5 hours
  2. extractionextracted from ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-d7869253a49043a1b675031e29f82c8d
Source dataset
uspto-grants-1997_11
Patent number
US05686458

Reaction notes

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