Ammonia → HCID 18975659, compound

HRID 2393121Notes

Reaction equation

HRID 2393121 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]([CH:14]2[CH2:17][CH2:16][CH2:15]2)=O)=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.N>C(#N)C>[CH:14]1([C:12]2[C:7]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=3)[CH2:9][CH2:10][N:11]=2)[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 18975689HCID 18975689, compound

Product 1

HCID 18975659HCID 18975659, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of this amide (9 g) in dry acetonitrile (170 ml) containing phosphorus oxychloride (23.7 ml) was heated under reflux for 43 hours. The cooled mixture was then poured onto dilute ammonia solution and this mixture extracted with ethyl acetate (3×150 ml). The ethyl acetate solution was then extracted with dilute hydrochloric acid (3×100 ml). The aqueous acid extracts were basified by addition of aqueous ammonia solution and the mixture extracted with ethyl acetate. The organic extracts were washed with brine and concentrated to give an oil which was distilled at 190° C./0.2 mbar to give 1-cyclobutyl-7-methoxy-3,4-dihydroisoquinoline as a colourless solid (4 g), mp 44°-46° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 43 hours
  3. extractionthis mixture extracted with ethyl acetate (3×150 ml)
  4. extractionThe ethyl acetate solution was then extracted with dilute hydrochloric acid (3×100 ml)
  5. additionThe aqueous acid extracts were basified by addition of aqueous ammonia solution
  6. extractionthe mixture extracted with ethyl acetate
  7. washThe organic extracts were washed with brine
  8. concentrationconcentrated
  9. customto give an oil which
  10. distillationwas distilled at 190° C./0.2 mbar

Sources & evidence

ORD record
ord-7806f9e008dd493ab92597370789d0f5
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Reaction notes

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