Lithium hydroxide, monohydrate → HCID 22918353, compound

HRID 1376754Notes

Reaction equation

HRID 1376754 reaction equation
C[O:2][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]([O:8]C)=[O:7].O.[OH-].[Li+]>CO.O>[NH:14]([C:12]1[CH:13]=[C:4]([C:3]([OH:28])=[O:2])[C:5](=[CH:10][C:11]=1[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:6]([OH:8])=[O:7])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10407176dimethyl 4,5-dianilinobenzene-1,2-dicarboxylate

Product 1

HCID 22918353HCID 22918353, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A steady stream of argon is passed through a suspension of 26.35 g (70.0 mmol) of 4,5-bis(anilino)phthalic acid dimethylester in 230 ml of methanol, and a solution of 11.78 g (280 mmol, 2 eq) of lithium hydroxide monohydrate in 116 ml of water is added. The reaction mixture is heated to reflux for 2.5 h, cooled to RT and diluted with 400 ml water. Methanol is removed by evaporation, the resulting solution is cooled to 0°, and 70 ml 4N hydrochloric acid are added. After 15 min. at 0°, the gray crystals are filtered off, washed with water and resuspended twice in 200 ml toluene with removal of the toluene by distillation to yield the title compound in the form of gray crystals, FAB-MS: 349 [M+ +H].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2.5 h
  3. customMethanol is removed by evaporation
  4. temperaturethe resulting solution is cooled to 0°
  5. addition70 ml 4N hydrochloric acid are added
  6. filtrationthe gray crystals are filtered off
  7. washwashed with water
  8. customresuspended twice in 200 ml toluene with removal of the toluene by distillation

Sources & evidence

ORD record
ord-a9e998fadeab4f659a0447833158b569
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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