Methylamine → HCID 10246831, compound

HRID 2396057Notes

Reaction equation

HRID 2396057 reaction equation
CO[C:3](=[O:28])[C:4]1[C:5](=[CH:10][C:11]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=1)[C:6](OC)=[O:7].[CH3:29][NH2:30]>C(O)CO>[NH:21]([C:11]1[CH:10]=[C:5]2[C:6](=[O:7])[N:30]([CH3:29])[C:3](=[O:28])[C:4]2=[CH:13][C:12]=1[NH:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10407176dimethyl 4,5-dianilinobenzene-1,2-dicarboxylate

Product 1

HCID 10246831HCID 10246831, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 376 mg (1 mmol) of 4,5-bis(anilino)phthalic acid dimethyl ester in 33 ml of ethylene glycol are heated at 120° and, with stirring, methylamine is passed through the mixture for 18 hours. Thereaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 1:1 and the product fractions are combined and concentrated by evaporation, yielding the title compound in the form of slightly yellow crystals, FAB-MS: 344 [M+ +H], m.p. 195°-196° C.

Workup

  1. temperatureThereaction mixture is cooled
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phases are washed in succession three times with water and once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed onsilica gel with hexane/ethyl acetate 1:1
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ff9cb10e95894585975d1a684f9fb1ab
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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