Ethylene Glycol → 2-(4-Amino-6-chloro-3-nitro-pyridin-2-yloxy)-ethanol

HRID 570232Notes

Reaction equation

HRID 570232 reaction equation
[H-].[Na+].Cl[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[C:8]([NH2:13])[CH:7]=[C:6]([Cl:14])[N:5]=1.[NH4+].[Cl-].[CH2:17]([OH:20])[CH2:18][OH:19]>>[NH2:13][C:8]1[CH:7]=[C:6]([Cl:14])[N:5]=[C:4]([O:19][CH2:18][CH2:17][OH:20])[C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2827402,6-Dichloro-3-nitropyridin-4-amine

Product 1

HCID 866574142-(4-Amino-6-chloro-3-nitro-pyridin-2-yloxy)-ethanol

Procedure

To a mixture of 60% sodium hydride in mineral oil (769 mg, 19.2 mmol) in ethylene glycol (10 mL) was added 2,6-dichloro-3-nitro-pyridin-4-ylamine (2.00 g, 9.62 mmol) slowly over 5 min. After stirring at room temperature for 16 h, the resulting mixture was treated with saturated NH4Cl (20 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with H2O (2×50 mL), brine (50 mL), and then dried over Na2SO4. The solvent was removed in vacuo and the resulting residue was triturated with hexanes. 2-(4-Amino-6-chloro-3-nitro-pyridin-2-yloxy)-ethanol was obtained as a light yellow solid (by filtration) and washed with hexanes. 1H-NMR (400 MHz, CD3OD) δ: 6.50 (s, 1H), 4.37-4.50 (m, 2H), 3.80-3.93 (m, 2H). Mass Spectrum (LCMS, ESI pos.) Calculated For C7H8ClN3O4: 234.0 (M+H), Measured: 234.0.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with H2O (2×50 mL), brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed in vacuo
  5. customthe resulting residue was triturated with hexanes

Sources & evidence

ORD record
ord-d512d88ea5984b1280b858718a6608d6
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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