Methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoate → Methyl 3-(3-cyanophenyl)-5-(4-aminophenyl)pentanoate

HRID 1586219Notes

Reaction equation

HRID 1586219 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:9]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)=[CH:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=2)[CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

3

Reactant 1

HCID 54059907Methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoate

Product 1

HCID 10781125Methyl 3-(3-cyanophenyl)-5-(4-aminophenyl)pentanoateYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part C. Methyl 3-(3-cyanophenyl)-5-(4-nitrophenyl)-2,4-pentadienoate (0.441 gm, 1.32 mmol) was dissolved in THF and degassed with N2. A catalytic amount of 10% Pd/C was added and the solution placed on a Parr shaker at 45 p.s.i. for 1 hour. After filtering through Celite, the solvent was removed under vacuum and the residue chromatographed on silica gel (10% ethyl acetate/methylene chloride) to yield methyl 3-(3-cyanophenyl)-5-(4-aminophenyl)pentanoate 0.220 gm (54%) of the product. MS: 309(M+H)+ ; 1H NMR (CDCl3): 1.9 (m, 2H), 2.35 (t, 2H), 2.6 (m, 2H), 3.15 (m, 1H), 3.55 (3H), 6. 60 (d, 2H), 6.85 (d, 2H), 7.5 (m, 4H).

Workup

  1. customdegassed with N2
  2. additionA catalytic amount of 10% Pd/C was added
  3. filtrationAfter filtering through Celite
  4. customthe solvent was removed under vacuum
  5. customthe residue chromatographed on silica gel (10% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-6e5473b30b8a4df0a70c643a48b574b9
Source dataset
uspto-grants-1999_08
Patent number
US05942544

Reaction notes

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