Water → HCID 56592002, compound

HRID 2404242Notes

Reaction equation

HRID 2404242 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=4)=[N:14][NH:13][C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32](I)[CH3:33].O>CN(C)C=O>[CH3:1][O:2][C:3]1[C:4]([O:24][CH3:25])=[CH:5][C:6]2[C:7]3[C:15]([C:16]4[CH:17]=[CH:18][C:19]([C:20]#[N:21])=[CH:22][CH:23]=4)=[N:14][N:13]([CH2:32][CH3:33])[C:8]=3[CH:9]=[N:10][C:11]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 54763438HCID 54763438, compound

Product 1

HCID 56592002HCID 56592002, compoundYield 34,000%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(7,8-Dimethoxy-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (132 mg, 400 μmol) is dissolved in N,N-dimethylformamide (5 ml). Potassium carbonate (111 mg, 800 μmol) and ethyl iodide (37 μl, 440 μmol) is subsequently added. The reaction mixture is stirred at room temperature for 3 h. The mixture is subsequently poured into water (100 ml) and extracted twice with ethyl acetate (100 ml each time). The combined organic phases are washed once with water (50 ml), dried over Na2SO4, filtered with suction, and the filtrate obtained is evaporated to dryness in vacuo. The residue is chromatographed over flash silica gel (solvent gradient n-heptane/0-100% by vol. of ethyl acetate/ethanol 0-30% by vol.). After evaporation of the product fractions, the residue is dissolved in a little tetrahydrofuran, and 2-propanol (5 ml) is added, and the mixture is evaporated. The precipitate obtained is filtered off with suction and dried in a high vacuum, giving the title compound 4-(7,8-dimethoxy-3-ethyl-3H-pyrazolo[3,4-c]quinolin-1-yl)benzonitrile (49 mg, 136 mmol) as a solid having a melting point of 227.4° C. MS: 359.0 (M+H+), TLC (HPTLC): Rf=0.51 (ethyl acetate/ethanol 8:1, parts by volume).

Workup

  1. extractionextracted twice with ethyl acetate (100 ml each time)
  2. washThe combined organic phases are washed once with water (50 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered with suction
  5. customthe filtrate obtained
  6. customis evaporated to dryness in vacuo
  7. customThe residue is chromatographed over flash silica gel (solvent gradient n-heptane/0-100% by vol. of ethyl acetate/ethanol 0-30% by vol.)
  8. customAfter evaporation of the product fractions
  9. dissolutionthe residue is dissolved in a little tetrahydrofuran, and 2-propanol (5 ml)
  10. additionis added
  11. customthe mixture is evaporated
  12. customThe precipitate obtained
  13. filtrationis filtered off with suction
  14. customdried in a high vacuum

Sources & evidence

ORD record
ord-d76e63f0646e4da29f7e353bf6b1cd5b
Source dataset
uspto-grants-2014_08
Patent number
US08802712B2

Reaction notes

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