Hydrochloric Acid → HCID 86692165, compound

HRID 2201758Notes

Reaction equation

HRID 2201758 reaction equation
[CH2:1]([CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[C:10](=[O:19])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO.C(OCC)(=O)C.O.O.O.O.O.O.[Co](Cl)Cl>[NH2:18][CH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:19])[NH:9][CH:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86692164HCID 86692164, compound

Product 1

HCID 86692165HCID 86692165, compoundYield 41.2%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-benzyl-1-oxoisoindoline-5-carbonitrile (190 mg, 0.77 mmol) in MeOH (4 mL) was added cobalt(II) chloride hexahydrate (364 mg, 1.53 mmol), then added NaBH4(232 mg, 6.12 mmol) in portions carefully within 45 min. The reaction mixture was stirred at room temperature for 30 min, TLC showed complete conversion. Carefully quenched reaction by adding concentrated HCl until the black precipitates dissolved. The reaction mixture was basified with concentrated NH4OH until pH=8-9, a brown colour slurry was obtained, diluted with ethyl acetate. This was filtered, for filtrate, washed 1× with water. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 5-10% MeOH in dichloromethane (0.5% NEt3 added), 80 mg (41%) of the product was obtained.

Workup

  1. customCarefully quenched reaction
  2. customblack precipitates
  3. dissolutiondissolved
  4. customa brown colour slurry was obtained
  5. filtrationThis was filtered, for filtrate
  6. washwashed 1× with water
  7. customThe organic phase was dried on Na2SO4
  8. customthe solvent was evaporated
  9. customThe residue was purified by flash-chromatography on silica gel with 5-10% MeOH in dichloromethane (0.5% NEt3 added)

Sources & evidence

ORD record
ord-22489dcf81174a7ca259a3ab82c35d48
Source dataset
uspto-grants-2016_06
Patent number
US09365512B2

Reaction notes

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