Methanol → HCID 22918363, compound

HRID 2396065Notes

Reaction equation

HRID 2396065 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].CO.[Li].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>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 4

HCID 887MethanolHCID 3028194LithiumHCID 18988109HCID 18988109, compoundHCID 23667548Sodium Ascorbate

Product 1

HCID 22918363HCID 22918363, compound

Reagents, catalysts & solvents 1

HCID 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 mlof methanol, and a solution of 101 mg (2.4 mmol, 4 eq) of lithium hydroxidemonohydrate 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-b97753b4de8744d8bbc460a6e247b052
Source dataset
uspto-grants-1996_02
Patent number
US05491144

Reaction notes

Loading…