HCID 23072445, compound → HCID 23072452, compound

HRID 1182485Notes

Reaction equation

HRID 1182485 reaction equation
[CH3:1][N:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-])=O)[C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)(=O)C.CO.[Ni]>[CH3:1][N:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH2:25])[C:3](=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 23072445HCID 23072445, compound

Product 1

HCID 23072452HCID 23072452, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of amide 87 (420 mg, 1.14 mmol) in a mixture of ethyl acetate and methanol (5 mL, 9:1) was added catalytic amount of a suspension of Raney Nickel. The mixture was stirred at room temperature under hydrogen pressure for 2 hours and then without pressure for 10 hours. The reaction mixture was filtered through a short pad of Celite and the solvents were removed in vacuo. Purification by flash silica gel chromatography (2% methanol in dichloromethane) afforded the corresponding amide 88 (180 mg, 47% yield). 1H NMR (300 MHz, CDCl3): δ 7.96-7.90 (m, 2H), 7.58-7.41 (2 m, 4H), 7.17-7.10 (m, 1H), 6.98 (dd, J=1.5, 7.5 Hz, 1H), 6.80-672 (m, 2H), 3.18 (s, 3H), 2.91 (t, J=7.2 Hz, 2H), 2.15-1.95 (m, 2H), 1.73-1.51 (m, 4H), 1.35-1.20 (m, 4H).

Workup

  1. additionwas added catalytic
  2. waitwithout pressure for 10 hours
  3. filtrationThe reaction mixture was filtered through a short pad of Celite
  4. customthe solvents were removed in vacuo
  5. customPurification by flash silica gel chromatography (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-90a0d88a305c4f3382119a270f9f5f1e
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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