Sulfuric acid magnesium salt (1:1) → HCID 70362883, compound

HRID 2073337Notes

Reaction equation

HRID 2073337 reaction equation
[CH:1]1[C:4]2[CH:5]=[CH:6][C:7]([N:9]3[C:13](=[O:14])[C:12]4=[CH:15][C:16]([N+:19]([O-])=O)=[CH:17][CH:18]=[C:11]4[C:10]3=[O:22])=[CH:8][C:3]=2[CH:2]=1.[O-]S([O-])(=O)=O.[Mg+2].[K+].[Br-]>[Pd].C(OCC)(=O)C>[CH:1]1[C:4]2[CH:5]=[CH:6][C:7]([N:9]3[C:13](=[O:14])[C:12]4=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=[C:11]4[C:10]3=[O:22])=[CH:8][C:3]=2[CH:2]=1

Participants

6

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 253877Potassium BromideHCID 19858390HCID 19858390, compound

Product 1

HCID 70362883HCID 70362883, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1.50 g (5.10 mmol) of N-4 benzocyclobutenyl-4-nitrophthalimide, 1.70 g of MgSO4, 0.2 g of 10% Pd/C and 60 ml of ethyl acetate were placed in a pressure bottle and the mixture was then rocked on a hydrogenator under initial hydrogen pressure of 60 psi for about 17 hrs. The resultant reaction mixture, which was yellow-green, was filtered through celite and the solid residue was washed with acetone until the filtrate was colorless. The combined yellow-green filtrate was stripped to dryness to provide greenish yellow product, which was collected on a fritted filter funnel, washed with petroleum ether and dried in vacuo overnight. Yield: 1.20 g (88.9%). The product was used in the subsequent reaction without further purification. Mass Spectroscopy: M+ (264 100%). IR (KBr plate): ν(NH2):3290 m, 3390 m cm-1 ; ν(CH2) 2860 w, 2940 m; ν(imide): 1773 ms, 1690 vs cm-1, δ(imide) 744 ms, 1HNMR (acetone): 2.93 ppm (s, broad 2H); 3.23 ppm (5.4 H): 7.45 (center, complex, 6 H).

Workup

  1. customfor about 17 hrs
  2. customThe resultant reaction mixture, which
  3. filtrationwas filtered through celite
  4. washthe solid residue was washed with acetone until the filtrate
  5. customto provide greenish yellow product, which
  6. customwas collected on a fritted filter funnel
  7. washwashed with petroleum ether
  8. customdried in vacuo overnight
  9. customThe product was used in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-21d954a6388a4aa7aae250e79b0c4d27
Source dataset
uspto-grants-1990_04
Patent number
US04916235

Reaction notes

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