4-Chlorobenzaldehyde → 5-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-one

HRID 874003Notes

Reaction equation

HRID 874003 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.[CH:20]1([C:23](=[O:32])[CH2:24][C:25](=[O:31])[C:26](OCC)=[O:27])C[CH2:21]1>C(O)(=O)C>[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[C:24]([C:23](=[O:32])[CH2:20][CH3:21])=[C:25]([OH:31])[C:26](=[O:27])[N:1]2[C:2]2[CH:3]=[C:4]([CH3:10])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 16779961Ethyl 4-cyclopropyl-2,4-dioxobutanoateHCID 674566165-Amino-1,3-dimethyl-1,2-dihydropyridin-2-one

Product 1

HCID 1177027685-(2-(4-chlorophenyl)-4-hydroxy-5-oxo-3-propionyl-2,5-dihydro-1H-pyrrol-1-yl)-1,3-dimethylpyridin-2(1H)-oneYield 68.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-amino-1,3-dimethylpyridin-2(1H)-one (Step 20.2) (1.77 g, 12.78 mmol), 4-chlorobenzaldehyde (1.63 g, 11.62 mmol) and ethyl 4-cyclopropyl-2,4-dioxobutanoate (2 g, 11.62 mmol) in acetic acid (10 mL) was stirred for 2 h at 100° C. The reaction mixture was concentrated, diluted with CH2Cl2/1 N NaOH, and extracted with CH2Cl2. The combined organic extracts were discarded. The aqueous layer was acidified to pH 3 with 6 N HCl and extracted twice with CH2Cl2. The combined organic extracts were dried (Na2SO4) and concentrated to afford 3.06 g of the title compound as a beige foam. tR. 0.83 min (LC-MS 2); ESI-MS: 387.0 [M+H]+ (LC-MS 2).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with CH2Cl2/1 N NaOH
  3. extractionextracted with CH2Cl2
  4. extractionextracted twice with CH2Cl2
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9196513fcaef419092beb822ea8a1382
Source dataset
uspto-grants-2015_03
Patent number
US08975417B2

Reaction notes

Loading…