Potassium Carbonate → HCID 66980583, compound

HRID 272665Notes

Reaction equation

HRID 272665 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4](I)[CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[NH2:24])[C:17]([O:19][CH3:20])=[O:18].C([O-])([O-])=O.[K+].[K+]>ClC1C=CC=CC=1.C(OCC)(=O)C.[Cu]>[NH2:13][C:14]1[CH:15]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[CH:21]=[CH:22][C:23]=1[NH:24][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 1355243,5-Diamino-2-methylbenzoic acidHCID 123491904-Chloro-2-iodo-benzoic acid Methyl ester

Product 1

HCID 66980583HCID 66980583, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-chloro-2-iodobenzoate (0.593 g, 2 mmol), methyl 3,4-diaminobenzoate (0.332 g, 2 mmol), copper (0.126 g, 2 mmol), and K2CO3 (0.276 g, 2 mmol) in chlorobenzene (40 mL) was heated to reflux for 20 hours, cooled to room temperature, diluted with ethyl acetate, and filtered through diatomaceous earth (Celite®). The solution was washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate to provide 0.453 g (68%) of the desired product. MS (DCI) m/e 334 (M+H)+, 352 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 8.99 (s, 1H), 7.89 (d, J=8.5 Hz, 1H), 7.47 (d, J=1.0 Hz, 1H), 7.21 (m, 2H), 6.80 (dd, J=8.5, 2.0 Hz, 1H), 6.65 (d, J=2.1 Hz, 1H), 5.30 (s, 2H), 3.86 (s, 3H), 3.82 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. washThe solution was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash column chromatography on silica gel with 7:3 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-2eafd1d4a7224dd79063bd5ee306e6b1
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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