N-(4-Bromophenyl)-5-chloro-2-nitrobenzamide → HCID 6481531, compound

HRID 844143Notes

Reaction equation

HRID 844143 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:4][CH:3]=1>CO.[Pt]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH2:17])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 4447365N-(4-Bromophenyl)-5-chloro-2-nitrobenzamide

Product 1

HCID 6481531HCID 6481531, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of N-(4-bromophenyl)-2-nitro-5-chlorobenzamide (0.50 g, 1.4 mmol) in methanol (20 mL) was added 5% platinum on carbon (Degussa type, 50% water, 0.20 g), and the mixture stirred under hydrogen (balloon). After 0.5 hours, the mixture was filtered and concentrated of all volatiles in vacuo to afford 0.45 g (99% yield) of N-(4-bromophenyl)-2-amino-5-chlorobenzamide as a white solid; NMR (DMSO-d6) 10.2 (s, 1), 7.5-7.7 (m, 5), 7.2 (dd, 1), 6.8 (d, 1) ppm.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationconcentrated of all volatiles in vacuo

Sources & evidence

ORD record
ord-bb5bad939b304a7ab85652705fdafb04
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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