HCID 21272461, compound → HCID 21272458, compound

HRID 1193540Notes

Reaction equation

HRID 1193540 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:20][CH2:21][O:22][CH3:23])[C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[N+:16]([O-])=O.[H][H]>[Pd].CO>[CH3:23][O:22][CH2:21][CH2:20][N:5]([CH2:4][CH2:3][O:2][CH3:1])[C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[NH2:16]

Participants

5

Reactant 2

HCID 21272461HCID 21272461, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 21272458HCID 21272458, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A two liter autoclave was charged with 65.0 g of N,N-bis(2-methoxyethyl)-2,4-dinitrobenzamide, 1000 ml of methanol and 2.7 g of a 5% palladium on carbon/50% water catalyst. The mixture was hydrogenated at 800 psi hydrogen pressure while maintaining the temperature between 60°-100° C. Hydrogen uptake ceased after 30 min. The mixture was cooled, filtered, and the methanol removed at reduced pressure to give 53.2 g of N,N-bis(2-methoxyethyl)-2,4-diaminobenzamide, a red-brown viscous liquid.

Workup

  1. temperaturewhile maintaining the temperature between 60°-100° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customthe methanol removed at reduced pressure

Sources & evidence

ORD record
ord-445b0859a64b4c3b94de1fd98d4eff05
Source dataset
uspto-grants-1989_03
Patent number
US04810769

Reaction notes

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