Sodium borohydride → HCID 70665245, compound

HRID 1615460Notes

Reaction equation

HRID 1615460 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[O:17][CH3:18]>CO.[Ni](Cl)Cl>[Cl:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=1[O:17][CH3:18]

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 66602053HCID 66602053, compound

Product 1

HCID 70665245HCID 70665245, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent2×

Procedure

Nickel chloride 6H2O (3.19 g, 13.4 mmol) was dissolved in methanol (20 mL) and celite (200 mg) was added and 1.5 eq (1.52 g, 40.18 mmol) of sodium tetrahydridoborate was added slowly portion wise. The slurry was stirred for 30 minutes at room temperature. The compound (7.5 g, 26.8 mmol) prepared in Example 6 dissolved in methanol was added slowly to the slurry. After addition, sodium tetrahydridoborate (3.55 g, 93.84 mmol) was slowly added portion wise. The reaction was then stirred for an hour at room temperature. The reaction was filtered through celite and the pad was washed with methanol (50 mL). The solvent was removed and the residue was taken up in hydrochloric acid (1N) and the aqueous layer was extracted with ethyl acetate. The combine organic layers were dried over anhydrous sodium sulfate, filtered and solvent was removed to leave a reddish solid. The solid was triturate with hexane to obtain the title compound (6.03 g) having the following physical data.

Workup

  1. additioncelite (200 mg) was added
  2. additionwas added slowly to the slurry
  3. stirringThe reaction was then stirred for an hour at room temperature
  4. filtrationThe reaction was filtered through celite
  5. washthe pad was washed with methanol (50 mL)
  6. customThe solvent was removed
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. dry with materialThe combine organic layers were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customsolvent was removed
  11. customto leave a reddish solid
  12. customThe solid was triturate with hexane

Sources & evidence

ORD record
ord-5c0b2571cc4a4bf19875165827fcceef
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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