Lithium hydroxide, monohydrate → HCID 22918419, compound

HRID 1376778Notes

Reaction equation

HRID 1376778 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[C:5](=[CH:10][C:11]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH3:24])[CH:13]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CO.O>[NH:25]([C:11]1[CH:10]=[C:5]([C:6]([OH:8])=[O:7])[C:4](=[CH:13][C:12]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=1[O:23][CH3:24])[C:3]([OH:32])=[O:2])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 23667548Sodium AscorbateHCID 54043359HCID 54043359, compound

Product 1

HCID 22918419HCID 22918419, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A steady stream of argon is passed through a suspension of 479 mg (1.09 mmol) of 4-anilino-5-(2,4-dimethoxy-anilino)phthalic acid dimethylester in 3.6 ml of methanol, and a solution of 205 mg (4.905 mmol, 4.5 eq) of lithium hydroxide monohydrate and 10 mg sodium ascorbate in 1.7 ml of water is added. The reaction mixture is heated to reflux for 4 hours, cooled to RT, and the methanol is removed by evaporation. The resulting mixture is poured onto 20 ml of 4N hydrochloric acid, the red suspension is filtered and the crystals are washed with washed with isopropanol/hexane 1:5 to yield the title compound in the form of red crystals, TLC (dichloromethane/methanol 7:3) Rf =0.33.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 4 hours
  3. customthe methanol is removed by evaporation
  4. additionThe resulting mixture is poured onto 20 ml of 4N hydrochloric acid
  5. filtrationthe red suspension is filtered
  6. washthe crystals are washed
  7. washwith washed with isopropanol/hexane 1:5

Sources & evidence

ORD record
ord-c16108dbfb4a4d45af389739048b0306
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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