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

HRID 1729683Notes

Reaction equation

HRID 1729683 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-2a345e0b77e044dfb8494aa212734e43
Source dataset
uspto-grants-1976_11
Patent number
US03989704

Reaction notes

Loading…