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

HRID 564948Notes

Reaction equation

HRID 564948 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 to 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-044ac79e764346b1873b3b34578791f4
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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