1-Nitropropane → HCID 90300729, compound

HRID 2272628Notes

Reaction equation

HRID 2272628 reaction equation
Cl[C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:15])/[CH:12]=C/C)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH2:16]1CCN2C(=NCCC2)C[CH2:17]1.[N+:27]([CH2:30][CH2:31][CH3:32])([O-:29])=O.[Cl-:33].[Na+].[OH2:35]>>[Cl:33][C:6]1[CH:5]=[C:4]([NH:10][C:11](=[O:15])[CH2:12][CH:31]([CH3:32])[CH:30]([N+:27]([O-:29])=[O:35])[CH2:16][CH3:17])[CH:3]=[CH:2][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 4

HCID 79031-NitropropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57417360Sodium chloride; waterHCID 86729778HCID 86729778, compound

Product 1

HCID 90300729HCID 90300729, compoundYield 84%

Procedure

A solution of the compound obtained in Step 1 of Example 48 (1.2 g, 5.44 mmol) and DBU (0.984 mL, 6.53 mmol) in 1-nitropropane (2.420 mL, 27.19 mmol) was stirred at 60° C. for 2 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; 10 to 30% ethyl acetate/hexane) to give N-(3-chloro-4-cyanophenyl)-3-methyl-4-nitrohexanamide (1.420 g, 4.58 mmol, 84%) as a pale-yellow oil.

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; 10 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-98f1401b8d8b427597d76c7180ec1b7a
Source dataset
uspto-grants-2015_09
Patent number
US09120776B2

Reaction notes

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