Tin tetrachloride → HCID 86600792, compound

HRID 716733Notes

Reaction equation

HRID 716733 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[N:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.[Sn](Cl)(Cl)(Cl)Cl>Cl>[ClH:5].[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([NH:12][NH2:1])=[CH:10][N:11]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 793055-Amino-2-chloropyridineHCID 23668193Sodium Nitrite

Product 1

HCID 86600792HCID 86600792, compoundYield 269.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

An aqueous sodium nitrite solution (3.49 g of sodium nitrite in 12.5 mL of water) was dropwise added to a solution of 6-chloropyridine-3-amine (5.00 g) in hydrochloric acid (77.8 mL) over 10 minutes (such that the temperature does not exceed −20° C.) under dry ice-acetone cooling (−20 to −40° C.), followed by stirring under the same conditions for 1 hour. A solution of tin chloride (14.8 g) in hydrochloric acid (25 mL) was dropwise added thereto over 15 minutes, followed by stirring at approximately 0° C. for 2 hours. The precipitated solid was collected by filtration (washed with water and n-hexane) and was vacuum dried at 40° C. to yield the title compound (9.45 g, brown solid).

Workup

  1. customdoes not exceed −20° C.
  2. customunder dry ice-acetone cooling (−20 to −40° C.)
  3. waitover 15 minutes
  4. stirringby stirring at approximately 0° C. for 2 hours
  5. filtrationThe precipitated solid was collected by filtration (washed with water and n-hexane)
  6. customdried at 40° C.

Sources & evidence

ORD record
ord-6aacac117e8b4e5caea24aebd9c4b5f0
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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