Ammonia → HCID 10066030, compound

HRID 2396055Notes

Reaction equation

HRID 2396055 reaction equation
CO[C:3](=[O:29])[C:4]1[C:5](=[CH:10][C:11]([N:21]([CH3:28])[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]([O:8]C)=O.[NH3:30]>C(O)CO>[CH3:28][N:21]([C:11]1[CH:10]=[C:5]2[C:6](=[O:8])[NH:30][C:3](=[O:29])[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:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10068965HCID 10068965, compound

Product 1

HCID 10066030HCID 10066030, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Analogously to Example 1, 160 mg (0.41 mmol) of 4-(N-methyl-N-phenylamino)-5-anilinophthalic acid dimethyl ester in 12 ml of ethylene glycol are heated at 120° and, with stirring, ammonia gas is passed through the mixture for 18 hours. The reaction mixture is cooled and extracted with ethyl acetate. The ethyl acetate phases are washed in succession three times with water and once with saturated sodiumchloride solution, dried with sodium sulfate and concentrated by evaporation. The evaporation residue is chromatographed on silica gel withhexane/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], 1H-NMR (CDCl3): 3.28 (s, 3H).

Workup

  1. temperatureThe reaction 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 sodiumchloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customThe evaporation residue is chromatographed on silica gel withhexane/ethyl acetate 1:1
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-47b3be500559475aae7ecaa9e1563cda
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

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