Ethyl Acetate → HCID 15224424, compound

HRID 274378Notes

Reaction equation

HRID 274378 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-])=O.S([O-])([O-])(=O)=O.[Mg+2].[H][H].[C:28]([O:31][CH2:32][CH3:33])(=O)[CH3:29]>[Pt]>[CH2:28]([O:31][CH2:32][C:33]1[N:6]([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[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)[CH3:29]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 9860004HCID 9860004, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15224424HCID 15224424, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Conditions

Temperature
120 °C

Procedure

4-(3-methoxypropylamino)-3-nitroquinoline (14.6 g; 0.056 mol, Example 41) was added to a mixture of ethyl acetate (1300 mL), 5% platinum on carbon (1.0 g), and magnesium sulfate (5.0 g). The mixture was hydrogenated on a Parr apparatus at an initial hydrogen pressure of 30 psi. When the hydrogenation was complete, the solids were removed and the ethyl acetate was evaporated. The residual intermediate diamine was mixed with ethoxyacetic acid (60 mL) and heated at 120° C. for about 8 hours. The reaction mixture was cooled to room temperature, poured into water, made basic with 6N sodium hydroxide and then extracted with ether (5×100 mL). The ether extracts were combined, dried with magnesium sulfate, then evaporated. The residue was purified by silica gel chromatography (20% methanol in ethyl acetate as eluent) to give 13.3 g of a green oil. This material was used in subsequent reactions.

Workup

  1. customthe solids were removed
  2. customthe ethyl acetate was evaporated
  3. additionThe residual intermediate diamine was mixed with ethoxyacetic acid (60 mL)
  4. temperatureThe reaction mixture was cooled to room temperature
  5. additionpoured into water
  6. extractionextracted with ether (5×100 mL)
  7. dry with materialdried with magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by silica gel chromatography (20% methanol in ethyl acetate as eluent)

Sources & evidence

ORD record
ord-c56dfbcc192c4429bdf62d34c9643f03
Source dataset
uspto-grants-1995_02
Patent number
US05389640

Reaction notes

Loading…