N,N-bis(2-methoxyethyl)-3-nitrobenzamide → HCID 22113167, compound

HRID 1900021Notes

Reaction equation

HRID 1900021 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:17][CH2:18][O:19][CH3:20])[C:6](=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1.[H][H]>[Pd].C(OCC)(=O)C>[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])[CH2:17][CH2:18][O:19][CH3:20])=[O:16]

Participants

5

Reactant 2

HCID 22113236N,N-bis(2-methoxyethyl)-3-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 22113167HCID 22113167, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N,N-bis(2-methoxyethyl)-3-nitrobenzamide (4.11 g) and palladium on charcoal (411 mg) in ethyl acetate (41 ml) was hydrogenated under 1 atmospheric pressure of hydrogen for 1 hour at ambient temperature. The catalyst was removed by filtration and washed with ethyl acetate, and the volatiles were removed in vacuo. The residue was purified with column chromatography eluting with dichloromethane-methanol to give 3-amino-N,N-bis(2-methoxyethyl)benzamide (3.62 g) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with ethyl acetate
  3. customthe volatiles were removed in vacuo
  4. customThe residue was purified with column chromatography
  5. washeluting with dichloromethane-methanol

Sources & evidence

ORD record
ord-1018c89cf9944ce2aac353ade7333e65
Source dataset
uspto-grants-1996_11
Patent number
US05574042

Reaction notes

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