Sodium sulfate decahydrate → HCID 9881269, compound

HRID 612452Notes

Reaction equation

HRID 612452 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl.[CH3:9][O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[C:13](=O)[N:14]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[C:15]2=O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:9][O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][N:14]([NH:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[CH2:15]2

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 19595133HCID 19595133, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9881269HCID 9881269, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of lithium aluminum hydride (9.96 g) in dry tetrahydrofuran (150 ml) was stirred at ambient temperature, under nitrogen, as 4-methoxy-2-(4-pyridinylamino)isoindole-1,3-dione hydrochloride monohydrate (17.0 g) was added in portions. The reaction mixture was stirred, under nitrogen, at ambient temperature overnight and sodium sulfate decahydrate was added in portions, with cooling. The precipitate was collected, washed with ethyl acetate, and the filtrate was evaporated. The residue was chromatographed on silica, eluting with 8-10% methanol-dichloromethane. The appropriate fractions were collected and concentrated. The residue was crystallized, then recrystallized from ethyl acetate to give 7.2 g (57%) of product, mp 144-146° C.

Workup

  1. additionwas added in portions
  2. temperaturewith cooling
  3. customThe precipitate was collected
  4. washwashed with ethyl acetate
  5. customthe filtrate was evaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with 8-10% methanol-dichloromethane
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated
  10. customThe residue was crystallized
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-47cd88c1d7b644deb2fb5585af104a7b
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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