4-Chloro-2-methylbenzaldehyde → 3-Chloro-5-[2-(4-chloro-2-methyl-phenyl)-4-hydroxy-3-isobutyryl-5-oxo-2,5-dihydro-pyrrol-1-yl]-benzonitrile

HRID 869057Notes

Reaction equation

HRID 869057 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:10])[CH:9]=1)[C:5]#[N:6].[Cl:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[C:14]([CH3:20])[CH:13]=1.C([O:23][C:24](=O)[C:25](=[O:32])[CH2:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])C>C(O)(=O)C>[Cl:10][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([N:1]2[C:24](=[O:23])[C:25]([OH:32])=[C:26]([C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[CH:16]2[C:15]2[CH:18]=[CH:19][C:12]([Cl:11])=[CH:13][C:14]=2[CH3:20])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 27576584-Chloro-2-methylbenzaldehydeHCID 3017501Ethyl 5-methyl-2,4-dioxohexanoateHCID 110300243-Amino-5-chlorobenzonitrile

Product 1

HCID 896110733-Chloro-5-[2-(4-chloro-2-methyl-phenyl)-4-hydroxy-3-isobutyryl-5-oxo-2,5-dihydro-pyrrol-1-yl]-benzonitrileYield 26.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-amino-5-chloro-benzonitrile (2.4 g, 15.7 mmol), 4-chloro-2-methyl-benzaldehyde (2.4 g, 15.7 mmol) and 5-methyl-2,4-dioxo-hexanoic acid ethyl ester (2.9 g, 15.7 mmol) in acetic acid (15 mL) was stirred at 120° C. for 16 h. The reaction mixture was allowed to cool to rt, concentrated, diluted with acetonitrile (15 mL), and stirred for 4 h at rt. The resulting precipitate was collected by vacuum filtration and dried to afford 1.8 g of the title compound. tR: 6.50 min (HPLC 2); ESI-MS: 429 [M+H]+ (LC-MS 2); Rf=0.27 (hexane/EtOAc, 1:1).

Workup

  1. temperatureto cool to rt
  2. concentrationconcentrated
  3. additiondiluted with acetonitrile (15 mL)
  4. stirringstirred for 4 h at rt
  5. filtrationThe resulting precipitate was collected by vacuum filtration
  6. customdried

Sources & evidence

ORD record
ord-89ea81c291b4447292b1423c55e3125f
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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