Ethylene Glycol → 2-(4-Amino-6-chloro-3-nitro-pyridin-2-yloxy)-ethanol
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
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
- extractionextracted with EtOAc (3×50 mL)
- washThe combined organic layers were washed with H2O (2×50 mL), brine (50 mL)
- dry with materialdried over Na2SO4
- customThe solvent was removed in vacuo
- customthe resulting residue was triturated with hexanes
Sources & evidence
- ORD record
- ord-5e3c2d91c0734952b0dfd08e12f54c9d
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409915B2
Reaction notes
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