Nitromethane → HCID 86729779, compound

HRID 2272621Notes

Reaction equation

HRID 2272621 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:15])/[CH:12]=[CH:13]/[CH3:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1CCN2C(=NCCC2)CC1.[N+:27]([CH3:30])([O-:29])=[O:28]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:15])[CH2:12][CH:13]([CH3:14])[CH2:30][N+:27]([O-:29])=[O:28])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86729778HCID 86729778, compound

Product 1

HCID 86729779HCID 86729779, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The compound obtained in Step 1 (21.69 g, 98.31 mmol), DBU (16.30 mL, 108.14 mmol) and nitromethane (6.00 g, 98.31 mmol) were stirred at room temperature for 14 hr. To the reaction solution was added brine at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 30% ethyl acetate/hexane) to give N-(3-chloro-4-cyanophenyl)-3-methyl-4-nitrobutanamide (21.20 g, 75 mmol, 77%) as a pale-orange powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-40f94f87774c4ff2b8f30007eaeb83dd
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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