Ammonia → HCID 22406798, compound

HRID 440514Notes

Reaction equation

HRID 440514 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P(Cl)(Cl)(Cl)=O.N>C(#N)C>[CH:16]1([C:14]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:8]([O:9][CH3:10])[CH:7]=3)[CH2:11][CH2:12][N:13]=2)[CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 9246054HCID 9246054, compound

Product 1

HCID 22406798HCID 22406798, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-[2-(3,4-dimethoxyphenyl)ethyl]cyclobutanecarboxamide (44 g, prepared in a similar manner to that described in Example E46), phosphorus oxychloride (150 ml) and acetonitrile (900 ml) was heated under reflux for 2.5 hours. The cooled solution was poured onto dilute aqueous ammonia solution and the product was extracted into ethyl acetate. The extracts were washed with brine, dried and the solvent removed in vacuo. The resulting oil solidified on standing for 16 hours. The solid was recrystallised from petroleum ether (b.p. 60°-80° C.) to give 1-cyclobutyl-3,4-dihydro-6,7-dimethoxyisoquinoline (20 g).

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated
  3. temperatureunder reflux for 2.5 hours
  4. extractionthe product was extracted into ethyl acetate
  5. washThe extracts were washed with brine
  6. customdried
  7. customthe solvent removed in vacuo
  8. customThe solid was recrystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-8f7bef756434499d9ced030bac439a39
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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