HCID 68952336, compound → HCID 68952090, compound

HRID 1887462Notes

Reaction equation

HRID 1887462 reaction equation
C([O:8][C:9]1[C:10]([O:39][CH3:40])=[CH:11][C:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][C:16]4[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[C:22]([O:29][C:30](=[O:37])[C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)[C:17]=4[CH2:18]3)[C:13]=2[CH:38]=1)C1C=CC=CC=1>[Ni].CO>[OH:8][C:9]1[C:10]([O:39][CH3:40])=[CH:11][C:12]2[CH2:21][CH2:20][N:19]3[CH:14]([CH2:15][C:16]4[C:25]([Cl:26])=[CH:24][C:23]([O:27][CH3:28])=[C:22]([O:29][C:30](=[O:37])[C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=5)[C:17]=4[CH2:18]3)[C:13]=2[CH:38]=1

Participants

4

Reactant 1

HCID 68952336HCID 68952336, compound

Product 1

HCID 68952090HCID 68952090, compoundYield 26.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A product obtained in Example 3 (0.183 g, 0.33 mmol) was add CH3OH (15 ml) and Raney-Ni. The mixture was hydrogenated at room temperature for 1 hours. The mixture was filtered, and the filtrate was concentrated to give the product as yellow-green solide (0.16 g). The solide was recrystallized with ethyl acetate/petroleum ether to give pale yellow powder (0.041 g, 26.7%). mp 162˜164° C. 1HNMR (CDCl3) δ: 2.57˜2.71 (3H, m, CH2), 3.08˜3.12 (2H, m, CH2), 3.36˜3.58 (3H, m, CH2 and N—CH), 3.79 (3H, s, Ar—OCH3), 3.87 (3H, s, Ar—OCH3), 4.02 (1H, br, CH2), 5.55 (1H, s, Ar—OH), 6.59 (1H, s, ArH), 6.89 (1H, s, ArH), 6.95 (1H, s, ArH), 7.51˜7.56 (2H, m, PhH), 7.65˜7.67 (1H, m, PhH), 8.22˜8.24 (2H, m, PhH). MS (EI) m/z: 464 (M−1), 360, 344, 178, 105 (base), 77.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give the product as yellow-green solide (0.16 g)
  4. customThe solide was recrystallized with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-2c3ce11e6fde474aa116875aed8640c9
Source dataset
uspto-grants-2013_08
Patent number
US08501762B2

Reaction notes

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