Sodium hydride → HCID 21309648, compound

HRID 1416662Notes

Reaction equation

HRID 1416662 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][OH:8].[H-].[Na+].[N+:11]([C:14]1[CH:15]=[N:16][CH:17]=[C:18]([N+]([O-])=O)[CH:19]=1)([O-:13])=[O:12]>CN(C=O)C.O.[Cl-].[Na+].O>[N+:11]([C:14]1[CH:19]=[C:18]([O:8][CH2:7][C@@H:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])[CH:17]=[N:16][CH:15]=1)([O-:13])=[O:12]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 978361-Methyl-2-pyrrolidinemethanolHCID 5980543,5-Dinitropyridine

Product 1

HCID 21309648HCID 21309648, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 23713072Sodium chloride dihydrateSolvent

Procedure

1-Methylpyrrolidinylmethanol (0.46 ml, 3.9 mmol) was added to a suspension of NaH in DMF at room temperature. After stirring at room temperature for 30 minutes, 3,5-dinitro-pyridine (0.34 g, 4 mmol) was added, and the mixture was allowed to stir at room temperature for 16 hours. The mixture was diluted with 1:1 water/brine, and the aqueous solution was extracted with ether. The combined ether layers were dried over MgSO4, filtered and concentrated. The residue was chromatographed, eluting with CH2Cl2 : methanol (10:0.5) to afford 70 mg of the title compound. MS (DCI/NH3) m/e: 238 (M+1). 1H NMR (CDCl3, 300MHz) δ: 9.06 (m, 1H), 8.62 (d, 1H), 7.97 (m, 1H), 4.07 (m, 2H), 3.50 (s, 3H), 3.13 (m, 1H), 2.73 (m, 1H), 2.35 (m, 1H), 2.05 (m, 1H), 1.82 (m, 3H).

Workup

  1. stirringto stir at room temperature for 16 hours
  2. extractionthe aqueous solution was extracted with ether
  3. dry with materialThe combined ether layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed
  7. washeluting with CH2Cl2 : methanol (10:0.5)

Sources & evidence

ORD record
ord-c1312ee9eb3f4b90a79c02de812bbc03
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

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