HCID 54133511, compound → HCID 928867, compound

HRID 1490287Notes

Reaction equation

HRID 1490287 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=O)[C:5]1=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-])=O)(=[O:3])[CH3:2]>[Pd].CCO>[C:1]([N:4]1[C:5]2[CH:14]=[C:15]3[C:16]([CH:17]=[CH:18][CH:19]=[CH:20]3)=[N:21][C:6]=2[C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 54133511HCID 54133511, compound

Product 1

HCID 928867HCID 928867, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-acetyl-2-(2-nitrophenyl methylene)-3-oxo-2,3-dihydroindole from Example 33 (220 mg, 0.71 mmol), 10% Pd/C (33 mg) and absolute EtOH (25 mL) was shaken on a Parr Shaker at 50 psi of H2 for 3 hours. The Pd catalyst was filtered off over a celite pad and the solvent was evaporated. The crude yellow product (209 mg, >100%) was purified by LPLC, eluting with hexane-EtOAc (2:1), to afford 92 mg (50%) of the title compound as a light yellow solid (90% pure by NMR) , Rf 0.38 (hexane-EtOAc 1:1), mp 163.2°-164.6° C. [(lit 177°-178° C. (Fichter, F.; Boehringer, R. Chem. Ber. 1906, 39, 3932)]; 1H NMR (CDCl3) δ 9.04 (s, 1H), 8.52 (d, J=8.0, 1H), 8.28 (d, J=8.8, 1H), 8.16 (d, J=8.4, 1H), 8.02 (d, J=8.4, 1H), 7.77 (m, 1H), 7.68 (m, 1H), 7.61 (m, 1H), 7.52 (m, 1H), 2.99 (s, 3H); 13C NMR (CDCl3) 169.7, 147.3, 145.9, 141.5, 137.5, 131.4, 130.6, 128.8, 128.6, 128.5, 127.3, 126.1, 124.4, 122.0, 121.6, 115.8, 27.6; MS (EI, m/z) 260 (M+) .

Workup

  1. filtrationThe Pd catalyst was filtered off over a celite pad
  2. customthe solvent was evaporated
  3. customThe crude yellow product (209 mg, >100%) was purified by LPLC
  4. washeluting with hexane-EtOAc (2:1)

Sources & evidence

ORD record
ord-1e4124d1bb1a4d1686bd7078f975123e
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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