Acetic Acid → N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamide

HRID 991426Notes

Reaction equation

HRID 991426 reaction equation
[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:30])=[C:14]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[N+:26]([O-])=O)[CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.[Fe]>[C:1]([NH:9][C:10]1[CH:11]=[CH:12][C:13]([Cl:30])=[C:14]([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=2[NH2:26])[CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 10340Sodium CarbonateHCID 22238139N-(5-benzamido-2-chlorophenyl)-4-methoxy-2-nitrobenzamide

Product 1

HCID 9908705N-(5-benzamido-2-chlorophenyl)-2-amino-4-methoxybenzamideYield 46%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (2.79 g) was added to a stirred suspension of N-(5-benzamido-2-chlorophenyl)-4-methoxy-2-nitrobenzamide (2.13 g) in a mixture of ethanol (100 ml), water (20 ml) and acetic acid (4 ml). The mixture was stirred and heated to reflux for 6 hours. The mixture was cooled to ambient temperature. Water (50 ml) was added and the resultant mixture was basified by the addition of sodium carbonate. The mixture was filtered and the filtrate was evaporated. The residue was triturated under water. The resultant solid was isolated and dried under vacuum at 40° C. There was thus obtained the title compound (0.911 g);

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was triturated under water
  6. customThe resultant solid was isolated
  7. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-496ac22ec8004cff908f5ec448e0236a
Source dataset
uspto-grants-2002_10
Patent number
US06465455B1

Reaction notes

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