Tetrahydrofuran → HCID 22646044, compound

HRID 393496Notes

Reaction equation

HRID 393496 reaction equation
[N+:1]([C:4]1[CH:26]=[C:25]([N+:27]([O-])=O)[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[O:12])=[CH:9][CH:8]=1)([O-])=O.C1COCC1.[H][H]>[Pd].[C].C(O)C>[NH2:1][C:4]1[CH:26]=[C:25]([NH2:27])[CH:24]=[CH:23][C:5]=1[O:6][C:7]1[CH:22]=[CH:21][C:10]([C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])=[O:12])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 22646056HCID 22646056, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22646044HCID 22646044, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1.55 g (3.90 mmol) of 4-(2,4-dinitrophenoxy)-2′-methylbenzanilide was dissolved into the solvent mixture with 70 ml THF and 30 ml of ethanol, and 0.166 g of 5% Pd-carbon powder was added into this solution. The solution was thoroughly deaerated under the reduced pressure at −78° C., and then stirred for 15 hours after the system was replaced with hydrogen gas and temperature was brought back to room temperature. The solution was concentrated after removing catalyst with Celite to yield 1.26 g of 4-(2,4-diaminophenoxy)-2′-methylbenzanilide shown in the structural formula (V) above in light brown solid (Yield: 96.7%).

Workup

  1. additionwas added into this solution
  2. customwas thoroughly deaerated under the reduced pressure at −78° C.
  3. customwas brought back to room temperature
  4. concentrationThe solution was concentrated
  5. customafter removing catalyst with Celite

Sources & evidence

ORD record
ord-41543210a3f147ce89aebe0071180666
Source dataset
uspto-grants-2004_10
Patent number
US06808766B1

Reaction notes

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