N-[5-[(Diethylamino)carbonyl]-2-nitrophenyl]-4-ethoxy-benzeneacetamide → HCID 22181390, compound

HRID 1796505Notes

Reaction equation

HRID 1796505 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([N+:25]([O-])=O)=[C:10]([NH:12][C:13](=[O:24])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH:11]=1)=[O:5])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:25][C:9]1[CH:8]=[CH:7][C:6]([C:4]([N:3]([CH2:1][CH3:2])[CH2:28][CH3:29])=[O:5])=[CH:11][C:10]=1[NH:12][C:13](=[O:24])[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH3:23])=[CH:19][CH:20]=1

Participants

4

Reactant 1

HCID 22181377N-[5-[(Diethylamino)carbonyl]-2-nitrophenyl]-4-ethoxy-benzeneacetamide

Product 1

HCID 22181390HCID 22181390, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-[5-[(Diethylamino)carbonyl]-2-nitrophenyl]4-ethoxy-benzeneacetamide (1.00 g, 2.50 mmol) was dissolved in EtOAc (50 mL) containing a catalytic amount of 10% Pd/C. The solution was shaken under H2 atmosphere (35 psi) at rt overnight. The solution was filtered through celite and the solvent was concentrated. LC/MS analysis showed that the title compound was pure enough (>95%) and could directly be used for next step. Yield: 927 mg (99%); 1HNMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.25 (d, J=7.6 Hz, 2H), 7.07 (s, 1H), 7.01 (d, J=8.0 Hz, 1H), 6.91 (d, J=7.2 Hz, 2H), 6.66 (d, J=8.4 Hz, 1H), 4.04 (q, J=6.8 Hz, 2H), 3.69 (s, 2H), 3.39 (br s, 4H), 1.42 (t, J=6.8 Hz, 3H), 1.15 (br s, 6H).

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-f0a0de53f2fc474798fc72cb194af0d1
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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