Lithium hydroxide, monohydrate → HCID 22918423, compound

HRID 1376759Notes

Reaction equation

HRID 1376759 reaction equation
C[O:2][C:3](=[O:30])[C:4]1[C:5](=[CH:10][C:11]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH:13]=1)[C:6]([O:8]C)=[O:7].O.[OH-].[Li+]>CO.O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:12]2[CH:13]=[C:4]([C:3]([OH:30])=[O:2])[C:5](=[CH:10][C:11]=2[NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[C:6]([OH:8])=[O:7])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10476762HCID 10476762, compound

Product 1

HCID 22918423HCID 22918423, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A steady stream of argon is passed through a suspension of 5.0 g (12.12 mmol) of 4,5-bis-(4-fluoroanilino)phthalic acid dimethylester in 40 ml of methanol, and a solution of 2.04 g (48.6 mmol, 2 eq) of lithium hydroxide monohydrate in 20 ml of water is added. The reaction mixture is heated to reflux for 1 hour, cooled to RT and diluted with 50 ml water. Methanol is removed by evaporation, the resulting solution is cooled to 0°, and 12 ml 4N hydrochloric acid and thereafter 100 ml of water are added. After 15 rain at 0°, the gray crystals are filtered off, washed with water and resuspended twice in 100 ml toluene with removal of the toluene by distillation to yield the title compound in the form of gray crystals, FAB-MS: 385 [M+ +H].

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 1 hour
  3. customMethanol is removed by evaporation
  4. temperaturethe resulting solution is cooled to 0°
  5. addition12 ml 4N hydrochloric acid and thereafter 100 ml of water are added
  6. filtrationAfter 15 rain at 0°, the gray crystals are filtered off
  7. washwashed with water
  8. customresuspended twice in 100 ml toluene with removal of the toluene by distillation

Sources & evidence

ORD record
ord-7654b146ca544f2ca3e1c4b1d199436e
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

Loading…