Ammonia → 1-Methyl-3,4-dihydroisoquinoline

HRID 1264890Notes

Reaction equation

HRID 1264890 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.N>>[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

3

Reactant 2

HCID 222AmmoniaHCID 70143N-(2-phenylethyl)acetamide

Product 1

HCID 2315021-Methyl-3,4-dihydroisoquinolineYield 97%

Conditions

Temperature
160 °C

Procedure

The compound (25.3 g, 154.8 mmol) prepared in Step 1 above was added to polyphosphoric acid (250 g) and then stirred for 1.5 hours at 160° C. The reaction mixture was poured into ice water, neutralized with ammonia solution, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was subjected to silica gel column chromatography (eluent: methanol/dichloromethane ={fraction (1/20)}) to give 21.8 g of the titled compound as an oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-010df0db772944dba327f3aadcc759ce
Source dataset
uspto-grants-2003_04
Patent number
US06545008B1

Reaction notes

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