HCID 22406836, compound → HCID 22406764, compound

HRID 440527Notes

Reaction equation

HRID 440527 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][NH:12][C:13]([C:15]2([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[CH2:17][CH2:16]2)=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>C(Cl)(Cl)Cl>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:15]1([C:13]2[C:5]3[C:4](=[CH:3][C:2]([F:1])=[C:7]([O:8][CH3:9])[CH:6]=3)[CH2:10][CH2:11][N:12]=2)[CH2:17][CH2:16]1

Participants

3

Reactant 1

HCID 22406836HCID 22406836, compound

Product 1

HCID 22406764HCID 22406764, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of N-[2-(3-fluoro-4-methoxyphenyl)ethyl]-1-(2,4-dichlorophenyl)cyclopropanecarboxamide (19.7 g, prepared in a similar manner to that described in Example E4), 52% polyphosphate ester in chloroform (200 g) was heated under reflux for 52 hours, then cooled and poured onto ice. The organic layer was separated, the aqueous layer extracted with dichloromethane and the combined organic layers were basified by addition of aqueous ammonia solution, washed with brine, dried over magnesium sulphate and filtered. The solvent was removed in vacuo to yield a solid which was triturated with petroleum ether (b.p. 40°-60° C.) and propan-2-ol. The solid was collected by filtration and dried to yield 1-[1-(2,4-dichlorophenyl)cyclopropyl]-6-fluoro-7-methoxy-3,4-dihydroisoquinoline (10.3 g), m.p. 151°-154° C.

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated
  3. temperatureunder reflux for 52 hours
  4. temperaturecooled
  5. additionpoured onto ice
  6. customThe organic layer was separated
  7. extractionthe aqueous layer extracted with dichloromethane
  8. additionthe combined organic layers were basified by addition of aqueous ammonia solution
  9. washwashed with brine
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. customThe solvent was removed in vacuo
  13. customto yield a solid which
  14. customwas triturated with petroleum ether (b.p. 40°-60° C.) and propan-2-ol
  15. filtrationThe solid was collected by filtration
  16. customdried

Sources & evidence

ORD record
ord-3c3600a53fd84f63baeb8c60fae63ca4
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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