Sodium borohydride → HCID 21075807, compound

HRID 1373895Notes

Reaction equation

HRID 1373895 reaction equation
[C:1](=[N:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:18])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([NH:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[C:6]1[CH3:18])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21075811HCID 21075811, compound

Product 1

HCID 21075807HCID 21075807, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-isopropylidene(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.82 g, 7.64 mmol) dissolved in 40 mL of MeOH was treated with NaBH4 (1.16 g, 30.6 mmol). After stirring for 18 h, the reaction was quenched with saturated NH4Cl solution and partitioned between CH2Cl2 and 2% Na2CO3 solution. The organic portion was washed with 2% Na2CO3 solution, H2O and brine and dried over Na2SO4. The resulting organic portion was filtered and concentrated under reduced pressure to give N-isopropyl(2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)amine (1.84 g) as a yellow foam.

Workup

  1. customthe reaction was quenched with saturated NH4Cl solution
  2. custompartitioned between CH2Cl2 and 2% Na2CO3 solution
  3. washThe organic portion was washed with 2% Na2CO3 solution, H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe resulting organic portion was filtered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8c65c9cc8f5c4e89a42f0ed34fb7c749
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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