Ethanol → 4,5-diamino-N-(4-bromophenyl)-2-methoxybenzamide

HRID 1410237Notes

Reaction equation

HRID 1410237 reaction equation
[NH2:1][C:2]1[C:17]([N+:18]([O-])=O)=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[O:7])=[C:4]([O:21][CH3:22])[CH:3]=1.C1COCC1.CCO>[Fe].CC(O)=O>[NH2:1][C:2]1[C:17]([NH2:18])=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[O:7])=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 595298014-amino-N-(4-bromophenyl)-2-methoxy-5-nitrobenzamide

Product 1

HCID 595298704,5-diamino-N-(4-bromophenyl)-2-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-N-(4-bromophenyl)-2-methoxy-5-nitrobenzamide (1.30 g; 3.55 mmol), THF (80 mL) and EtOH (50 mL) was treated with AcOH (3 mL) and stirred for 15 min at 100° C. To the warm mixture, Fe (1.30 g; 23.3 mmol) was carefully added in portions and the resulting mixture was heated for 2 h at 100° C. The mixture was cooled, filtered through celite and concentrated to give the crude sub-title compound.

Workup

  1. temperaturethe resulting mixture was heated for 2 h at 100° C
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through celite and
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a0844971eb6649cab1a32e785d9089e5
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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