HCID 23507821, compound → HCID 23507801, compound

HRID 1377085Notes

Reaction equation

HRID 1377085 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:28])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:28])[CH2:11][CH2:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:14])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 23507821HCID 23507821, compound

Product 1

HCID 23507801HCID 23507801, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of dodecyl 4-(4-nitrophenyl)-4-oxobutyrate (0.42 g, 1.1 mmol), in ethyl acetate (50 ml) and 10% palladium on carbon (0.10 g) were shaken under hydrogen (30-40 psi) for 10 minutes. The mixture was filtered and the filtrate concentrated in vacuo to give dodecyl 4-(4-aminophenyl)-4-oxobutyrate (0.38 g) as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ: 0.86 (t, J=6.5 Hz, 3H, ester CH3), 1.10-1.37 (m, 18H, ester CH2 's), 1.47-1.60 (m, 2H, ester CH2), 2.57 (t, J=6.5 Hz, 2H, CH2), 3.10 (t, J=6.5 Hz, 2H, CH2), 3.98 (t, J=6.5 Hz, 2H, ester CH2), 6.04 (br s, 2H, NH2), 6.56 (d, J=8.5 Hz, 2H, Ar), 7.68 (d, J=8.5 Hz, 2H, Ar). Anal. Calculated for C22H35NO3.1/20 H2O: C, 72.91; H, 9.76; N, 3.86. Found: C, 72.86; H, 9.83; N, 3.82.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-f56eb5fa7c5c4146a6d2b95abb235038
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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