Sodium Carbonate → 4,5-Dichloropyridin-2-amine

HRID 323558Notes

Reaction equation

HRID 323558 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]([NH:9]C(=O)C(C)(C)C)[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:9][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 10538422N-(4,5-Dichloropyridin-2-yl)pivalamide

Product 1

HCID 107733044,5-Dichloropyridin-2-amineYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Compound 8 (10 g, 0.04 mol) in 6 N HCl (50 mL) was heated at reflux for 10 h. This solution was neutralized with Na2CO3 (to pH 7 by litmus) and then extracted with EtOAc (3×150 mL). The combined EtOAc extracts were dried over magnesium sulfate, filtered and concentrated to give a solid residue, which, after recrystallization from EtOH, gave 6.3 g (97%) of compound 4 as a white solid (mp 140-141° C.).

Workup

  1. temperatureat reflux for 10 h
  2. extractionextracted with EtOAc (3×150 mL)
  3. dry with materialThe combined EtOAc extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a solid residue, which
  7. customafter recrystallization from EtOH

Sources & evidence

ORD record
ord-1ebc28f80fbd4695a64465c6e85ebfd6
Source dataset
uspto-grants-2001_04
Patent number
US06214801B1

Reaction notes

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