4-Chlorobenzaldehyde → 4-acetyl-5-(4-chlorophenyl)-3-hydroxy-1-[(4-methoxyphenyl)methyl]-2,5-dihydro-1H-pyrrol-2-one

HRID 873926Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=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:8]([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=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 754524-Methoxybenzylamine

Product 1

HCID 1177028964-acetyl-5-(4-chlorophenyl)-3-hydroxy-1-[(4-methoxyphenyl)methyl]-2,5-dihydro-1H-pyrrol-2-one

Procedure

The title compound was prepared in analogy to the procedure described in Step 57.1 using 4-methoxybenzylamine, 4-chlorobenzaldehyde and ethyl 2,4-dioxovalerate at 120° C. for 3 hr. The title product precipitated at RT. tR: 4.90 min (HPLC 1); tR: 1.03 min (LC-MS 2); ESI-MS: 372 [M+H]+, ESI-MS: 370 [M−H]− (LC-MS 2).

Workup

customThe title product precipitated at RT

Sources & evidence

ORD record: ord-1ba38a5ec68244cea8971ebda594022b
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975417B2

Reaction notes

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