Methanol → HCID 16065352, compound

HRID 240305

Reaction equation

HRID 240305 reaction equation
[O:1]=[C:2]1[C:14]2[C:9](=[N:10][C:11](C#N)=[C:12]([C:15]#[N:16])[N:13]=2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[BH4-].[Na+].[OH2:21].[CH3:22]O>>[OH:1][CH:2]1[C:14]2[C:9](=[N:10][C:11]([O:21][CH3:22])=[C:12]([C:15]#[N:16])[N:13]=2)[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 2929299-oxo-9H-indeno(1,2-b)pyrazine-2,3-dicarbonitrileHCID 4311764Sodium borohydride

Product 1

HCID 16065352HCID 16065352, compoundYield 53%

Conditions

Temperature
0 °C

Procedure

To a suspension of 1 (150 mg, 0.646 mmol) in MeOH (6.5 ml), cooled at 0° C., NaBH4 (24 mg, 0.646 mmol) was added. After 30 min, water (5 ml) was added, MeOH was evaporated and the residue was extracted with CH2Cl2 (3×5 ml). The organic layers were dried over Na2SO4, filtered and evaporated. EtOH was added and the precipitate was collected by filtration affording 2 (82 mg, 53%) as white solid.

Workup

  1. customMeOH was evaporated
  2. extractionthe residue was extracted with CH2Cl2 (3×5 ml)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. additionEtOH was added
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-53bbcc47733a4da5a71f65262cc9e700
Source dataset
uspto-grants-2014_02
Patent number
US08648076B2

Linked notes

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