HCID 22254478, compound → HCID 12114241, compound

HRID 1611788Notes

Reaction equation

HRID 1611788 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-])=O>[Pt].C(OCC)(=O)C>[O:17]([CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[NH2:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 1

HCID 22254478HCID 22254478, compound

Product 1

HCID 12114241HCID 12114241, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-Nitro-N-(2-phenoxyethyl)quinolin-4-amine (6.0 g, 19 mmol), 5% platinum on carbon (1.5 g) and ethyl acetate (300 ml) were placed in a hydrogenation flask. The mixture was shaken overnight under a hydrogen pressure of 40 psi (2.8 Kg/cm2). The reaction mixture was filtered and the catalyst was washed with ethyl acetate. The filtrate was dried (MgSO4), filtered, and concentrated under vacuum to near dryness. Hexane was added and the resulting precipitate was collected by vacuum filtration to provide 4.9 g of N4-(2-phenoxyethyl)quinoline-3,4-diamine as a pale yellow solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe catalyst was washed with ethyl acetate
  3. dry with materialThe filtrate was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionHexane was added
  7. filtrationthe resulting precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-a158e9f4d7f24eb5a2f09a6c341a486f
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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