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

HRID 1693413Notes

Reaction equation

HRID 1693413 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-0f5cdbe84f0849c39b64d5990120a8ca
Source dataset
uspto-grants-2012_04
Patent number
US08158622B2

Reaction notes

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