Ethyl 4-(4-nitrophenyl)-4-oxobutanoate → ethyl 4-(4-aminophenyl)-4-oxobutanoate

HRID 2289270Notes

Reaction equation

HRID 2289270 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1)([O-])=O>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:18])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 15535281Ethyl 4-(4-nitrophenyl)-4-oxobutanoate

Product 1

HCID 232338ethyl 4-(4-aminophenyl)-4-oxobutanoateYield 30.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 4-(4-nitrophenyl)-4-oxobutyrate (1.4 g, 5.6 mmol) and 10% palladium on carbon (0.18 g) in ethanol (50 ml) was shaken under hydrogen (50 psi) for 2 hours then filtered and concentrated in vacuo. The residue was absorbed onto silica gel (5 g) from an ethyl acetate solution and purified by chromatography on silica gel (10 g) eluting with ethyl acetate:hexane (1:2) to give ethyl 4 -(4-aminophenyl)-4-oxobutyrate (0.38 g) as a white solid. 4NMR (DMSO-d6, 300 MHz) δ: 1.17 (t, J=7 Hz, 3H, CH3), 2.56 (t, J=6.5 Hz, 2H, CH2), 3.10 (t, J=6.5 Hz, 2H, CH2), 4.04 (q, J=7 Hz, 2H, ester CH2), 6.04 (br s, 2H, NH2), 6.57 (d, J=9 Hz, 2H, Ar), 7.69 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C12H15NO3 : C, 65.14; H, 6.83; N, 6.33. Found: C, 65.23; H, 6.85; N, 6.32.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed onto silica gel (5 g) from an ethyl acetate solution
  4. custompurified by chromatography on silica gel (10 g)
  5. washeluting with ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-2c23d9bc605a4acf9bce034703d7df82
Source dataset
uspto-grants-2000_07
Patent number
US06090941

Reaction notes

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