4-Chlorobenzaldehyde → HCID 178458262, compound

HRID 1418056Notes

Reaction equation

HRID 1418056 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH2:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15](=O)[C:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=O)[CH2:2][CH3:3].C([O-])(=O)C.[NH4+:29].[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1.[OH-].[NH4+:40]>C(O)(=O)C.C(OCC)(=O)C>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([C:35]2[NH:29][C:16]([C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)=[C:15]([C:6]3[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH2:13][CH3:14])=[CH:10][C:5]=3[O:4][CH2:1][CH2:2][CH3:3])[N:40]=2)=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 77264-ChlorobenzaldehydeHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 53632863HCID 53632863, compound

Product 1

HCID 178458262HCID 178458262, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2,4-di-n-propyloxyphenyl)-2-(4-pyridyl)ethane-1,2-dione from Step D (61 mg, 0.19 mmol), ammonium acetate (144 mg, 1.87 mmol) and 4-chlorobenzaldehyde (33 mg, 0.23 mmol) in acetic acid (1.5 mL) was heated to 100° C. for 3.5 h. After cooling to 0° C., the ice (4g), ethyl acetate (2 mL) and a concentrated solution of ammonium hydroxide was added until the pH was 10. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organic extracts were successively washed with water and saturated salt solution and dried over anhydrous sodium sulfate. The mixture was filtered and the solvent removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-3% methanol in methylene chloride to yield the title compound as a cream-colored solid (25 mg, 30% yield), mass spectrum (CI) m/e=448 (M+1)+.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with ethyl acetate
  3. washThe combined organic extracts were successively washed with water and saturated salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvent removed by rotoevaporation
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluted with 0-3% methanol in methylene chloride

Sources & evidence

ORD record
ord-dea4770b36114084b3806b9f609720f1
Source dataset
uspto-grants-1999_03
Patent number
US05880139

Reaction notes

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