Lithium hydroxide, monohydrate → HCID 66688686, compound

HRID 1020394Notes

Reaction equation

HRID 1020394 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=1)[C:6]2=[O:15].O.[OH-].[Li+]>C1COCC1>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]2[C:3]=1[CH2:4][N:5]([CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[C:6]2=[O:15]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66688964HCID 66688964, compound

Product 1

HCID 66688686HCID 66688686, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-((4-bromo-5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl)benzoate (500 mg, 1.19 mmol) in the step 2 and lithium hydroxide monohydrate (199 mg, 4.76 mmol, 4 equiv.) were dissolved in a mixture of THF and distilled water (mixture ratio=2:1 (v/v), 10 mL), and stirred at room temperature for 1 night. The reaction proceeded until no starting material is detectable by TLC. The resulting mixture thus obtained was distilled under a reduced pressure to remove THF. The resulting material was dissolved in distilled water and 1N HCl was added thereto to be pH 2. White precipitates thus obtained were filtered and dried under vacuum to obtain the title compound (380 mg, 78%).

Workup

  1. distillationdistilled water (mixture ratio=2:1 (v/v), 10 mL)
  2. customThe resulting mixture thus obtained
  3. distillationwas distilled under a reduced pressure
  4. customto remove THF
  5. dissolutionThe resulting material was dissolved in distilled water
  6. addition1N HCl was added
  7. customWhite precipitates thus
  8. customobtained
  9. filtrationwere filtered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-b4645e65cebd4a3586bfd7b38fb4d635
Source dataset
uspto-grants-2014_05
Patent number
US08716326B2

Reaction notes

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