4-Chlorobenzaldehyde → HCID 117702570, compound

HRID 873905Notes

Reaction equation

HRID 873905 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.[O:20]=[C:21]([CH2:27][C:28](=[O:30])[CH3:29])[C:22](OCC)=[O:23]>CC(O)=O>[C:28]([C:27]1[CH:16]([C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][CH:14]=2)[N:1]([C:2]2[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)[C:22](=[O:23])[C:21]=1[OH:20])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 69208Ethyl 2,4-dioxovalerateHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 117702570HCID 117702570, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

A round-bottomed flask was charged 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2) (3 g, 21.71 mmol), 4-chlorobenzaldehyde (2.348 g, 16.70 mmol) and ethyl 2,4-dioxovalerate (3.17 g, 20.04 mmol) in AcOH (50 mL) and the reaction mixture was heated up and stirred at 125° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, quenched with a saturated aq. NaHCO3 solution, extracted with EtOAc. The organic layer was discarded and the aq. phase was adjusted to pH 1-2, extracted EtOAc. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure to afford the title product (3.82 g, 8.71 mmol, 52% yield) as a black solid. tR: 3.54 min (HPLC 1); tR: 0.75 min (LC-MS 2); ESI-MS: 373 [M+H]+ (LC-MS 2).

Workup

  1. temperaturethe reaction mixture was heated up
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customquenched with a saturated aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. extractionextracted EtOAc
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b748a12a5a454e35a749aac5c3198b17
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

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