Nitromethane → HCID 22236902, compound

HRID 1743977Notes

Reaction equation

HRID 1743977 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([CH3:14])=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[N+:15]([CH3:18])([O-:17])=[O:16].C1CCN2C(=NCCC2)CC1>C(#N)C>[CH3:14][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH2:18][N+:15]([O-:17])=[O:16])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 69594025Ethyl 3-(pyridin-2-yl)but-2-enoate

Product 1

HCID 22236902HCID 22236902, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6 g of the compound obtained in Step 1, 3.36 ml of nitromethane and 4.26 ml of DBU dissolved in 120 ml of acetonitrile was heated to reflux for 36 hours. After the reaction was completed, the reaction solution was distilled under reduced pressure. The residue thus obtained was purified by a silica gel column chromatography using a mixture of ethyl acetate and n-hexane of 1:9 to obtain 1.8 g of the title compound as a syrup.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 36 hours
  3. distillationthe reaction solution was distilled under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by a silica gel column chromatography
  6. additiona mixture of ethyl acetate and n-hexane of 1:9

Sources & evidence

ORD record
ord-995470827d67461cbbf0be5af4c91273
Source dataset
uspto-grants-2006_03
Patent number
US07012144B2

Reaction notes

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