Nitrous Acid → HCID 21393854, compound

HRID 1288464Notes

Reaction equation

HRID 1288464 reaction equation
N[C:2]1[C:3]([Cl:12])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.N([O-])=O.[Na+].N(O)=O.[H+].[B-](F)(F)(F)[F:22]>>[Cl:12][C:3]1[C:2]([F:22])=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[CH:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 24529Nitrous AcidHCID 28118Tetrafluoroboric acidHCID 213938438-Isoquinolinamine,7-chloro-(9CI)HCID 23668193Sodium Nitrite

Product 1

HCID 21393854HCID 21393854, compound

Procedure

8-Amino-7-chloroisoquinoline (0.005 mole), prepared as in Example 12, in 40% fluoboric acid (30 ml.) is cooled to -10° C. and diazotized with finely powdered sodium nitrite (3.5 g.). After 30 minutes, the reaction mixture is tested for nitrous acid with starch/iodide paper as described in Example 15. When a positive reaction is obtained, the reaction mixture is washed with small portions of ether and then agitated with a mixture of ethanol and ether (20 ml. each). The diazonium tetrafluoroborate is filtered, washed with ether, dried in vacuo and decomposed on an oil bath at approximately 150° C. The residue is partitioned between ether and 5% aqueous sodium hydroxide solution. The ether phase and extracts are combined, washed with water, dried over sodium sulfate and evaporated to yield 7-chloro-8-fluoroisoquinoline.

Workup

  1. customWhen a positive reaction
  2. customis obtained
  3. washthe reaction mixture is washed with small portions of ether
  4. filtrationThe diazonium tetrafluoroborate is filtered
  5. washwashed with ether
  6. customdried in vacuo
  7. customdecomposed on an oil bath at approximately 150° C
  8. customThe residue is partitioned between ether and 5% aqueous sodium hydroxide solution
  9. washwashed with water
  10. dry with materialdried over sodium sulfate
  11. customevaporated

Sources & evidence

ORD record
ord-728fd92027cd496fb6d6d78c6ebc44c5
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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