Hydrochloric Acid → HCID 15550707, compound

HRID 840556Notes

Reaction equation

HRID 840556 reaction equation
NC1([N+]([O-])=O)C=CC(Cl)=NC1[CH2:9][CH:10]([OH:12])[CH3:11].[C:16]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)(N1C=CN=C1)=[O:17].[ClH:28].[CH2:29]1[CH2:33]OCC1>>[Cl:28][C:24]1[N:25]=[C:26]2[C:27](=[CH:33][CH:29]=1)[NH:23][C:16](=[O:17])[O:12][C:10]2([CH3:11])[CH3:9]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 682631,1'-CarbonyldiimidazoleHCID 22457515HCID 22457515, compound

Product 1

HCID 15550707HCID 15550707, compoundYield 56%

Procedure

To a solution of 1-(3-amino-6-chloro-3-nitro-pyridin-2-yl)-propan-2-ol (0.3 g, 1.67 mmol) in anhydrous THF (20 mL) was added a solution of 1,1′-carbonyldiimidazole (0.68 g, 4.12 mmol) in anhydrous THF (10 mL). The reaction mixture was heated under reflux for 3 h. The reaction mixture was treated with 0.5N HCl, washed with brine, H2O, dried (MgSO4), concentrated and crystallized from EtOAc/hexane to obtain the title compound as a white crystalline solid (0.2 g, 56%): mp 175-178° C. 1H NMR( DMSO-d6) δ1.60 (s, 6H), 7.30 (d, 1H, J=8.41 Hz), 7.41 (d, 1H, J=8.41 Hz), 10.47 (s, 1H); MS((+)APCI) m/z 213 (M+H)+; Anal. Calc. For C9H9ClN2O2: C, 50.84; H, 4.27; N, 13.17. Found: C, 50.99; H, 4.28; N, 12.98.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. washwashed with brine, H2O
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customcrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-3e3196c8b9ba456487a6d7ad20143cac
Source dataset
uspto-grants-2002_04
Patent number
US06369056B1

Reaction notes

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