4-Chlorobenzaldehyde → 5-(4-chlorophenyl)-3-hydroxy-4-(2-methoxyacetyl)-1-(4-methoxybenzyl)-1H-pyrrol-2(5H)-one

HRID 873990Notes

Reaction equation

C[O:2][CH2:3][C:4](=[O:13])[CH2:5][C:6](=[O:12])[C:7]([O:9][CH2:10]C)=O.[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>>[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]2[N:30]([CH2:29][C:28]3[CH:31]=[CH:32][C:25]([O:24][CH3:23])=[CH:26][CH:27]=3)[C:3](=[O:2])[C:4]([OH:13])=[C:5]2[C:6](=[O:12])[CH2:7][O:9][CH3:10])=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 77264-Chlorobenzaldehyde

HCID 754524-Methoxybenzylamine

HCID 67172400Ethyl 5-methoxy-2,4-dioxopentanoate

Product 1

HCID 1177025905-(4-chlorophenyl)-3-hydroxy-4-(2-methoxyacetyl)-1-(4-methoxybenzyl)-1H-pyrrol-2(5H)-one

Conditions

Temperature: 120 °C

Procedure

The title compound was prepared using an analogous procedure to that described in Step 57.1 but using equimolar amounts of ethyl 5-methoxy-2,4-dioxopentanoate (Step 130.1), 4-chlorobenzaldehyde, and 4-methoxybenzylamine. The reaction mixture was stirred for 2 h at 120° C. and allowed to cool to rt. The precipitate was collected by filtration to provide the title compound (5.21 g) as a colorless solid. tR: 0.94 min (LC-MS 2); ESI-MS: 402.1 [M+H]+ (LC-MS 2).

Workup

customThe title compound was prepared
temperatureto cool to rt
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-ddce6b7c7b8e47db81d4121fd281433c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975417B2

Reaction notes

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