HCID 22567546, compound → HCID 22567521, compound

HRID 564913Notes

Reaction equation

HRID 564913 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH3:17])[C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1>C(OCC)(=O)C.[Pt](=O)=O>[NH2:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=1)[C:6]([N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH3:17])=[O:16]

Participants

4

Reactant 1

HCID 22567546HCID 22567546, compound

Product 1

HCID 22567521HCID 22567521, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of N-(2-methoxyethyl)-N-methyl-3-nitrobenzamide (840 mg) in ethyl acetate (8 ml) was added platinum dioxide (160 mg) and the resulting heterogeneous mixture was stirred under hydrogen atmosphere for 8 hours. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate to give 3-amino-N-(2-methoxyethyl)-N-methylbenzamide (761 mg) as a brown viscous oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-9a80cc494d9d457f9a94dfa9deda2b41
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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