2-Aminopyridine → HCID 90408903, compound

HRID 2177607Notes

Reaction equation

HRID 2177607 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Cl:10][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15](Cl)[CH:14]=[C:13]([CH3:21])[N:12]=1.[NH4+].[Cl-]>C1COCC1>[Cl:10][C:11]1[C:16]([N+:17]([O-:19])=[O:18])=[C:15]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:14]=[C:13]([CH3:21])[N:12]=1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 90408903HCID 90408903, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-aminopyridine (361 mg, 3.72 mmol) in THF (30 mL) was added 60% sodium hydride (164 mg, 4.09 mmol). After stirring for 2 h at rt, 2,4-dichloro-6-methyl-3-nitropyridine (864 mg, 4.09 mmol) was added. After stirring 3.5 h additional at rt, sat. NH4Cl solution (30 mL) was added. The organic layer was separated and the water layer was extracted with CH2Cl2 two times. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated. Chromatography on silica gel (0-30% ethyl acetatehexanes) provided the desired product (366 mg, 37%). MS (ESI) mass calcd. C11H9ClN4O2, 264.04. m/z found, 265.1 [M+H]+. 1H NMR (500 MHz, CDCl3) δ 8.51 (br s, 1H), 8.39 (ddd, J=5.0, 1.9, 0.7, 1H), 8.32 (s, 1H), 7.71 (ddd, J=8.2, 7.4, 1.9, 1H), 7.07 (ddd, J=7.4, 5.0, 0.9, 1H), 6.93 (dt, J=8.2, 0.8, 1H), 2.53 (s, 3H).

Workup

  1. stirringAfter stirring 3.5 h additional at rt
  2. customThe organic layer was separated
  3. extractionthe water layer was extracted with CH2Cl2 two times
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-235894d8118b4a80a37f12d3e45753d2
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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