4-Chlorobenzaldehyde → 5-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one

HRID 873907Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([Cl: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]>>[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]([Cl: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

Reactant 3

HCID 77264-Chlorobenzaldehyde

HCID 69208Ethyl 2,4-dioxovalerate

HCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-one

Product 1

HCID 1177027635-(3-acetyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-3-chloro-1-methyl-pyridin-2(1H)-one

Procedure

The title compound was prepared in analogy to the procedure described in Step 57.1 using 5-amino-3-chloro-1-methylpyridin-2(1H)-one (Step 5.2), 4-chlorobenzaldehyde and ethyl 2,4-dioxovalerate at 120° C. for 1 hr. tR: 3.73 min (HPLC 1); tR: 0.74 min (LC-MS 2); ESI-MS: 393/395 [M+H]+ (LC-MS 2).

Sources & evidence

ORD record: ord-9a0e10cc9b0647b48ba1a81976a9345a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975417B2

Reaction notes

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