Hydrochloric Acid → HCID 22918393, compound

HRID 1376782Notes

Reaction equation

HRID 1376782 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[C:5](=[CH:10][C:11]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:12]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[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+].Cl>CO.O>[NH:27]([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]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=1)[C:3]([OH:34])=[O:2])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 23667548Sodium AscorbateHCID 54183230HCID 54183230, compound

Product 1

HCID 22918393HCID 22918393, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A steady stream of argon is passed through a suspension of 245 mg (0.5 mmol) of 4-anilino-5-(3,4,5-trimethoxy-anilino)phthalic acid dimethylester in 1.6 ml of methanol, and a solution of 94.4 mg (2.25 mmol, 4.5 eq) of lithium hydroxide monohydrate and 10 mg sodium ascorbate in 0.8 ml of water is added. The reaction mixture is heated to reflux for 17 hours and then cooled to RT. The resulting mixture is treated dropwise with 0.5 ml of 4N hydrochloric acid, the green suspension is filtered, and the crystals are washed with water to yield the title compound in the form of green crystals, m.p. 145°-6° C., FAB-MS: 439 [M+ +H].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 17 hours
  3. filtrationthe green suspension is filtered
  4. washthe crystals are washed with water

Sources & evidence

ORD record
ord-87ec0f53dfb348558d8dd0ed8ffabd2b
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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