N-(6-chloro-3-iodopyridin-2-yl)pivalamide → 2-Amino-6-chloro-3-iodopyridine

HRID 751668Notes

Reaction equation

HRID 751668 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8]C(=O)C(C)(C)C)[C:5]([I:15])=[CH:4][CH:3]=1>Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([I:15])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 45480364N-(6-chloro-3-iodopyridin-2-yl)pivalamide

Product 1

HCID 454803652-Amino-6-chloro-3-iodopyridine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of N-(6-chloro-3-iodopyridin-2-yl)-2,2-dimethyl propionamide (Preparation 108, 5.0 g, 14.8 mmol) in 1M HCl was heated to reflux for 4.5 h. The reaction was cooled to rt and then extracted with diethyl ether (2×50 mL). The organics were washed with Na2CO3 solution (2×50 mL) before being dried (MgSO4) and the solvent removed in vacuo. Purification by column chromatography (SiO2, CH2Cl2) afforded the title compound. δH (CDCl3): 7.76 (1H, d), 6.46 (1H, d), 5.43–5.20 (2H, br s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4.5 h
  3. extractionextracted with diethyl ether (2×50 mL)
  4. washThe organics were washed with Na2CO3 solution (2×50 mL)
  5. dry with materialbefore being dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customPurification by column chromatography (SiO2, CH2Cl2)

Sources & evidence

ORD record
ord-833b5ae97186420fad5ac642f4b9ec37
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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