Acetic Acid → HCID 22316014, compound

HRID 541561Notes

Reaction equation

HRID 541561 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=O)/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C(O)(=O)C>CN(C)C=O.[Pd]>[CH2:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])[CH2:11][CH2:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=1)[NH2:19]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 6147378NSC171304

Product 1

HCID 22316014HCID 22316014, compoundYield 5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2E)-1,3-bis(3-nitrophenyl)prop-2-en-1-one (2.8 g, 0.0094 mol) in N,N-dimethylformamide (20 mL) was added 10% (by wt.) palladium on carbon and acetic acid (2.0 mL). The mixture was degassed with vacuum and purged with hydrogen three times before shaking on a Parr shaker for 72 hours under a hydrogen atmosphere. The mixture was filtered through celite, evaporated and purified by preparative LCMS (pH 10) to give the desired product (101 mg, 5%). LCMS for C15H19N2 (M+H)+: m/z=227.2.

Workup

  1. customThe mixture was degassed with vacuum
  2. custompurged with hydrogen three times
  3. filtrationThe mixture was filtered through celite
  4. customevaporated
  5. custompurified by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-5d64af4f7e78430c9de28baab75a2c78
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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