5-Amino-2-chloropyridine → HCID 86600792, compound

HRID 602743Notes

Reaction equation

HRID 602743 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[N:9]([O-])=O.[Na+].O.O.[Sn](Cl)(Cl)(Cl)Cl>Cl>[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 793055-Amino-2-chloropyridineHCID 23668193Sodium NitriteHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 86600792HCID 86600792, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To 0.5 g (3.9 mmol) of 6-chloro-pyridin-3-ylamine in 6 mL of 12M HCl at −20° C. were added a solution of 0.36 g (5.2 mmol, 1.3 eq) of sodium nitrite dissolved in 2 mL of H20. The reaction mixture was stirred for 15 min, and 4.4 g (19.5 mmol, 5 eq) of tin chloride dihydrate dissolved in 2 mL of 12M HCl were added. The reaction mixture was allowed to reach 0° C. within 40 min, and the white precipitate was recovered by filtration and washed with Et2O to yield 0.35 g (62%) of (6-chloro-pyridin-3-yl)-hydrazine hydrochloride as a white solid, MS: 144 (MH+).

Workup

  1. dissolutiondissolved in 2 mL of H20
  2. additionwere added
  3. waitto reach 0° C. within 40 min
  4. filtrationthe white precipitate was recovered by filtration
  5. washwashed with Et2O

Sources & evidence

ORD record
ord-24fa16e79f334b7f8284040577a22e4b
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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