Phosphorus oxychloride → 3-Tert.butyl-1-chloro-4-phenyl isoquinoline

HRID 46813Notes

Reaction equation

HRID 46813 reaction equation
[C:1]([C:5]1[NH:6][C:7]([C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)([Cl:24])=O>>[C:1]([C:5]1[N:6]=[C:7]([Cl:24])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 20385868HCID 20385868, compound

Product 1

HCID 203858433-Tert.butyl-1-chloro-4-phenyl isoquinoline

Procedure

A mixture of 11 g. (0.04 mole) of 3-tert. butyl-4-phenyl isocarbostyril and 40 ml. of phosphorous oxychloride is refluxed for one hour. The excess solvent is removed in vacuo and ice is added to the residue and stirred. The resulting solid is filtered and washed with water and recrystallized from ethanol to give 3-tert.butyl-1-chloro-4-phenyl isoquinoline; m.p. 139°-140° C.

Workup

  1. additionA mixture of 11 g
  2. customThe excess solvent is removed in vacuo and ice
  3. additionis added to the residue
  4. filtrationThe resulting solid is filtered
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-91424567741c4842a2b92cc0a20d01cd
Source dataset
uspto-grants-1979_11
Patent number
US04175191

Reaction notes

Loading…