3-Butyl-6-nitro-phthalide → 6-Amino-3-butyl-phthalide

HRID 2120178Notes

Reaction equation

HRID 2120178 reaction equation
[CH2:1]([CH:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-])=O)=[CH:12][CH:13]=2)[C:7](=[O:8])[O:6]1)[CH2:2][CH2:3][CH3:4]>C(O)C.[Pd]>[NH2:15][C:11]1[CH:10]=[C:9]2[C:14]([CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[O:6][C:7]2=[O:8])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 232745183-Butyl-6-nitro-phthalide

Product 1

HCID 98777066-Amino-3-butyl-phthalide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 141 g (0.6 mol) of compound obtained in Example 1 in 250 ml of ethanol there are added 14 g of 5% Pd—C catalyst. The mixture is hydrogenated at a pressure of 34 kg/cm2. After the absorption of hydrogen has ceased, the hot mixture is filtered to remove the catalyst. The filter cake is washed with hot ethanol. On cooling, the crystals are separated and additional product is obtained from the condensed filtrate and washed to give the title compound.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe hot mixture is filtered
  3. customto remove the catalyst
  4. washThe filter cake is washed with hot ethanol
  5. temperatureOn cooling
  6. customthe crystals are separated
  7. customadditional product is obtained from the condensed filtrate
  8. washwashed

Sources & evidence

ORD record
ord-54f752deb0374c2e9a75c176ee09be1e
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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