Hydrochloric Acid → HCID 21393803, compound

HRID 1288467Notes

Reaction equation

HRID 1288467 reaction equation
N[C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.[ClH:16].N([O-])=O.[Na+].[OH-].[Na+]>O>[Cl:16][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 21393852HCID 21393852, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21393803HCID 21393803, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

8-Amino-7-trifluoromethylisoquinoline (0.7 g.) in 2 ml. of concentrated hydrochloric acid and 10 ml. of water is diazotized at 0° C. with 0.25 g. of sodium nitrite in 5 ml. of water. The resulting solution is added to a solution of 2 g. of cuprous chloride in 20 ml. of concentrated hydrochloric acid previously warmed to 70° C. After standing overnight, the reaction mixture is basified with 10% aqueous sodium hydroxide solution and extracted with ether. The ether extracts are washed with water, dried over sodium sulfate and evaporated to give 8-chloro-7-trifluoromethylisoquinoline as the residue. This isoquinoline is converted to the hydrochloride and recrystallized from ethanol and ether.

Workup

  1. customis diazotized at 0° C. with 0.25 g
  2. additionThe resulting solution is added to a solution of 2 g
  3. extractionextracted with ether
  4. washThe ether extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-43854b115bb841d4825f2b35521964ea
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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