Hydrochloric Acid → HCID 10659117, compound

HRID 1866230Notes

Reaction equation

HRID 1866230 reaction equation
[Na].C(O[C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:16]#[N:17].Cl>CCO>[CH2:9]([O:8][C:6](=[O:7])[C:5](=[O:11])[CH2:12][C:13]1[CH:14]=[C:15]([C:16]#[N:17])[CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 28014343-Methyl-4-nitrobenzonitrileHCID 5360545Sodium

Product 1

HCID 10659117HCID 10659117, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Dissolve sodium metal (0.345 g) in absolute EtOH (25 mL), add diethyloxalate (10 mL) and then add 3-methyl-4-nitrobenzonitrile (1a, m=0, 1.6 g, Aldrich) as an EtOH solution (25 mL). Stir reaction mixture at rt for 16 h, neutralize the reaction by addition of 5N HCl (3 mL) and remove the EtOH under reduced pressure. Partition the residue between CH2Cl2 (100 mL) and H2O (50 mL). Wash the organic layer successively with H2O (50 mL) and brine (50 mL), dry (MgSO4) and concentrate to give a crude oil. Purify the oil by chromatography on SiO2 (cyclohexane-EtOAc, 70-30 v/v) to give after drying (40° C., house vacuum), the title compound (1.2 g) as yellow crystals.

Workup

  1. customreaction mixture at rt for 16 h
  2. customthe reaction
  3. customremove the EtOH under reduced pressure
  4. customPartition the residue between CH2Cl2 (100 mL) and H2O (50 mL)
  5. washWash the organic layer successively with H2O (50 mL) and brine (50 mL)
  6. dry with materialdry (MgSO4)
  7. concentrationconcentrate
  8. customto give a crude oil
  9. customPurify the oil by chromatography on SiO2 (cyclohexane-EtOAc, 70-30 v/v)
  10. customto give
  11. customafter drying (40° C., house vacuum)

Sources & evidence

ORD record
ord-4ad6dd92ada64febb2d09b241e0147f8
Source dataset
uspto-grants-2009_12
Patent number
US07629376B2

Reaction notes

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