O-Phenylenediamine → HCID 66980711, compound

HRID 272672Notes

Reaction equation

HRID 272672 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4](Cl)[CH:3]=1.[C:12]1([NH2:19])[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=1>ClC1C=CC=CC=1.[Cu]>[Br:1][C:2]1[CH:10]=[CH:9][C:5]2[C:6](=[O:8])[NH:19][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 1088294-Bromo-2-chlorobenzoic acid

Product 1

HCID 66980711HCID 66980711, compoundYield 41.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 4-bromo-2-chlorobenzoic acid (2.35 g, 10 mmol), 1,2-benzenediamine (1.08 g, 10 mmol) and copper (0.63 g, 10 mmol) in chlorobenzene (150 mL) was heated to reflux for 48 hours and filtered. The filter cake was washed with ethyl acetate several times. The combined filtrates were concentrated under vacuum and the residue was purified by flash column chromatography on silica gel with 8:2 hexanes/ethyl acetate to provide 1.20 g (22%) of the desired product. MS (DCI) m/e 289 (M+H)+, 307 (M+NH4)+; 1H NMR (500 MHz, DMSO-d6) δ 9.90 (s, 1H), 8.02 (s, 1H), 7.62 (d, J=8.4 Hz, 1H), 7.24 (d, J=1.8 Hz, 1H), 7.06 (dd, J=8.4, 1.8 Hz, 1H), 6.92-6.95 (m, 5H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 48 hours
  3. filtrationfiltered
  4. washThe filter cake was washed with ethyl acetate several times
  5. concentrationThe combined filtrates were concentrated under vacuum
  6. customthe residue was purified by flash column chromatography on silica gel with 8:2 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-4f50cba83b5946839e7f5d5ea8dd914d
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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