6-Amino-3-butyl-5-nitro-phthalide → 5,6-Diamino-3-butyl-phthalide

HRID 2120191Notes

Reaction equation

HRID 2120191 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:12][CH2:13][CH2:14][CH3:15])[O:7][C:8]2=[O:9])=[CH:4][C:3]=1[N+:16]([O-])=O.[H][H]>C(O)C.[Ni]>[NH2:16][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[NH2:1])[C:8](=[O:9])[O:7][CH:6]2[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 234391186-Amino-3-butyl-5-nitro-phthalideHCID 178418361HCID 178418361, compound

Product 1

HCID 234391215,6-Diamino-3-butyl-phthalide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 3.75 g (15 mmol) of compound obtained in Example 22 in 150 ml of 95% ethanol there is added Raney nickel catalyst to hydrogenate at a hydrogen pressure of 1 kg/cm2. After the absorption of hydrogen has ceased, the catalyst is filtered off, and the filtrate is concentrated to dryness. The residue is crystallised from dilute ethanol, giving the title product.

Workup

  1. customAfter the absorption of hydrogen
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated to dryness
  4. customThe residue is crystallised from dilute ethanol

Sources & evidence

ORD record
ord-4e5c8472d63e408cadda75bf8fb62825
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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