HCID 54252549, compound → HCID 21217866, compound

HRID 1586221Notes

Reaction equation

HRID 1586221 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([CH:16]=[CH:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=2)=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]([CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=2)[CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 54252549HCID 54252549, compound

Product 1

HCID 21217866HCID 21217866, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part C. Methyl 3-(3-nitrophenyl)-5-(4-cyanophenyl)-2,4-pentadienoate (0.869 gm, 2.6 mmol) was dissolved in THF and degassed with N2. A catalytic amount of 10% Pd/C was added and the solution was placed on a Parr shaker for 45 min. at 45 p.s.i. The solution was filtered through Celite and the solvent was removed under vacuum. The residue was chromatographed on silica gel eluting ethyl acetate:methylene chloride (20:80, v:v) to give methyl 3-(3-aminophenyl)-5-(4-cyanophenyl)pentanoate as an oil 0.512 gm (64%). 1H NMR (CDCl3): 1.9 (m, 2H), 2.55 (t, 2H), 3.0 (m, 1H), 3.25 (m, 2H), 3.6 (s, 3H), 6.5 (s, 1H), 6.55 (m, 2H), 7.1 (t, 1H), 7.3 (m, 2H), 7.55 (m, 3H).

Workup

  1. customdegassed with N2
  2. additionA catalytic amount of 10% Pd/C was added
  3. filtrationThe solution was filtered through Celite
  4. customthe solvent was removed under vacuum
  5. customThe residue was chromatographed on silica gel
  6. washeluting ethyl acetate:methylene chloride (20:80, v:v)

Sources & evidence

ORD record
ord-6ab44ed730af4f23a089e251f9a2a81b
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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