Sodium borohydride → HCID 21075788, compound

HRID 1373923Notes

Reaction equation

HRID 1373923 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([N:18]=[CH:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][CH2:4][C:5]1[N:6]([NH:18][CH2:19][CH2:20][CH:21]([CH3:22])[CH3:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 69176562HCID 69176562, compound

Product 1

HCID 21075788HCID 21075788, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(3-methylbutylidene)amine (1.28 g, 4.13 mmol) in 25 mL of methanol was treated with NaBH4 (0.47 g, 12.39 mmol). After 1 h, the reaction was quenched with saturated NH4Cl solution and the mixture was concentrated under reduced pressure. The residue was partitioned between CHCl3 and saturated NaHCO3 solution and the phases were separated The organic portion was washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield N-(2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)(3-methylbutyl)amine (1.24 g) as a dark orange oil.

Workup

  1. customthe reaction was quenched with saturated NH4Cl solution
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between CHCl3 and saturated NaHCO3 solution
  4. customthe phases were separated The organic portion
  5. washwas washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f40a499b58c4ab7a67fa2ac420b90e7
Source dataset
uspto-grants-2007_01
Patent number
US07163947B2

Reaction notes

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