Water → HCID 59651929, compound

HRID 2042600Notes

Reaction equation

HRID 2042600 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.[NH:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[NH2:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:10][CH2:11][C:12](=[O:14])[N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 766134-Methoxy-gamma-oxobenzenebutanoic acidHCID 786452-Hydrazinopyridine

Product 1

HCID 59651929HCID 59651929, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 1 neck round bottom flask equipped with a Dean-Stark trap and condenser, 4-(4-methoxyphenyl)-4-oxo-butyric acid (5.0 g, 20 mmol), 2-hydrazinopyridine (3.9 g, 36 mmol) and p-toluene sulfonic acid (0.3 g) in 100 mL benzene were heated to reflux for 2 h while water was removed. The reaction was cooled to rt, an equal volume of Et2O was added and the product collected; Mp>300° C. This solid was dissolved in HOAc (50 mL) and heated at 100° C. for 6 h. The reaction was concentrated, dissolved in EtOAc and washed with saturated NaHCO3 solution, water, NaCl solution and dried (MgSO4). The solvent was concentrated to a thick oil; MS m/z 282 (M+H).

Workup

  1. temperaturewere heated
  2. customwas removed
  3. additionan equal volume of Et2O was added
  4. customthe product collected
  5. dissolutionThis solid was dissolved in HOAc (50 mL)
  6. temperatureheated at 100° C. for 6 h
  7. concentrationThe reaction was concentrated
  8. dissolutiondissolved in EtOAc
  9. washwashed with saturated NaHCO3 solution, water, NaCl solution
  10. dry with materialdried (MgSO4)
  11. concentrationThe solvent was concentrated to a thick oil

Sources & evidence

ORD record
ord-a8ce63b1d3b541129988f7e47a7c7c7a
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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