Lithium hydroxide, monohydrate → HCID 22918363, compound

HRID 1376780Notes

Reaction equation

HRID 1376780 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[C:5](=[CH:10][C:11]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=2[O:34][CH3:35])=[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>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([O:32][CH3:33])[CH:30]=[CH:31][C:26]=1[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:36])=[O:2]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 18988109HCID 18988109, compoundHCID 23667548Sodium Ascorbate

Product 1

HCID 22918363HCID 22918363, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A steady stream of argon is passed through a suspension of 260 mg (0.6 mmol) of 4,5-bis(2,4-dimethoxy-anilino)phthalic acid dimethylester in 2 ml of methanol, and a solution of 101 mg (2.4 mmol, 4 eq) of lithium hydroxide monohydrate and 10 mg sodium ascorbate in 1 ml of water is added. The reaction mixture is heated to reflux for 10 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, FAB-MS: 469 [M+ +H].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 10 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-1ce3fe56d4e14e8aadf2e57df298de96
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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