Hydrochloric Acid → HCID 10624338, compound

HRID 2394346Notes

Reaction equation

HRID 2394346 reaction equation
[H-].[Na+].[C:3]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:15])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].Cl[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][C:28]([C:34]([F:37])([F:36])[F:35])=[CH:27][N:26]=1.Cl>COCCOC.C1(C)C=CC=CC=1>[CH2:8]([O:7][C:5]([CH:4]([C:3]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[C:25]1[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][C:28]([C:34]([F:35])([F:36])[F:37])=[CH:27][N:26]=1)=[O:6])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 84754Dibenzyl malonateHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 10624338HCID 10624338, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

In a dry flask was placed sodium hydride as a 60% suspension in oil (800 mg, 2.0 mmol). Most of the oil was removed by washing twice with hexanes. The remaining solid sodium hydride was then suspended in dry 1,2-dimethoxyethane (DME) (20 mL). A solution of dibenzyl malonate (5.0 mL, 2.0 mmol) in DME (15 mL) was then added dropwise with stirring. The mixture was stirred at room temperature for 0.5 hr after which a solution of 2-chloro-3-nitro-5-trifluoromethyl pyridine (2.3 g, 10.2 mmol) in DME (15 mL) was added. Stirring at room temperature was continued overnight and the reaction mixture was poured into ice/water. Following acidification to pH 3 with 1N HCl solution, the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to leave an oil. This was subjected to flash chromatography on silica gel using toluene as eluant. All fractions containing the desired product were combined and concentrated to leave a tan solid; 3.8 g (79%): mp 82°-84° C.

Workup

  1. customIn a dry flask was placed
  2. customMost of the oil was removed
  3. washby washing twice with hexanes
  4. additionwas added
  5. stirringStirring at room temperature
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto leave an oil

Sources & evidence

ORD record
ord-648d268d008f4feb9ad848647ecd6051
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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