Nitrogen → HCID 69032420, compound

HRID 2251874Notes

Reaction equation

HRID 2251874 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[N+:21]([O-])=O)[C:12]2=[O:24])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].N#N>CO.[Pd]>[NH2:21][C:17]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:18]=1[C:19](=[O:20])[N:11]([C:8]1[CH:9]=[CH:10][C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:6][CH:7]=1)[C:12]2=[O:24]

Participants

5

Reactant 2

HCID 947NitrogenHCID 238479702-[4-(1,1-Dimethylethyl)phenyl]-4-nitro-1H-isoindole-1,3(2H)-dione

Product 1

HCID 69032420HCID 69032420, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 100 mL round bottomed flask, 2-(4-tert-butyl-phenyl)-4-nitro-isoindole-1,3-dione (980 mg, 3.02 mmol) was dissolved in MeOH (30 mL). To this was added 10% Pd/C (100 mg) under a stream of N2. The flask was purged of oxygen and subjected to a balloon of H2 for 2 h. The reaction was filtered through a bed of Celite®, and the resulting filter cake was washed with EtOH. The filtrate was concentrated to a yellowish residue which was subjected to flash chromatography over silica gel eluting with 20% EtOAc in hexanes to give a yellow foam. MS (ES+): 295.2 (M+H)+.

Workup

  1. customThe flask was purged of oxygen
  2. filtrationThe reaction was filtered through a bed of Celite®
  3. filtrationthe resulting filter cake
  4. washwas washed with EtOH
  5. concentrationThe filtrate was concentrated to a yellowish residue which
  6. customto give a yellow foam

Sources & evidence

ORD record
ord-c4ecf48411e14d66adaab6d83f0a3cbd
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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