HCID 15233569, compound → HCID 69439836, compound

HRID 1029581Notes

Reaction equation

HRID 1029581 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[N+:26]([O-])=O)=[CH:16][CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:29])[CH:3]=1.[H][H]>C(O)C.[Pd]>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:29])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 15233569HCID 15233569, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69439836HCID 69439836, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.340 g (0.88 mmol) of the product of Step 1 in 15 mL of absolute ethanol was added 35 mg of 10% palladium on carbon catalyst and the mixture was hydrogenated at 40 psi of hydrogen on a Parr apparatus. Reduction was complete after 1.5 hours and the reaction mixture was filtered and evaporated in vacuo to afford a tan solid (0.300 g, 95%) which was used in the subsequent step without further purification: NMR (CDCl3) δ1.33 (t, J=10 Hz, 3H), 2.59 (s, 3H), 2.64 (s, 3H), 2.84 (q, J=10 Hz, 2H), 3.70 (br s, 2H), 5.48 (s, 2H), 6.70-6.82 (m, 2H), 6.90 (s, 1H), 7.03-7.22 (m, 4H), 7.36 (d, J=10 Hz, 2H); MS (FAB) m/e 357 (MH +).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-83c9071dacc741e7ba183c9ec0a9e1b8
Source dataset
uspto-grants-1992_04
Patent number
US05102880

Reaction notes

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