4-Methoxybenzylamine → 5-(4-Chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1-(4-methoxy-benzyl)-1,5-dihydro-pyrrol-2-one

HRID 869060Notes

Reaction equation

HRID 869060 reaction equation
C(O[C:4](=[O:13])[C:5](=[O:12])[CH2:6][C:7](=[O:11])[CH:8]([CH3:10])[CH3:9])C.[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[C:27]([CH3:33])[CH:26]=1>C(O)(=O)C.C(#N)C>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]2[N:21]([CH2:20][C:19]3[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=3)[C:4](=[O:13])[C:5]([OH:12])=[C:6]2[C:7](=[O:11])[CH:8]([CH3:9])[CH3:10])=[C:27]([CH3:33])[CH:26]=1

Participants

6

Reactant 3

HCID 754524-MethoxybenzylamineHCID 27576584-Chloro-2-methylbenzaldehydeHCID 3017501Ethyl 5-methyl-2,4-dioxohexanoate

Product 1

HCID 896111145-(4-Chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1-(4-methoxy-benzyl)-1,5-dihydro-pyrrol-2-oneYield 73%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

5-Methyl-2,4-dioxo-hexanoic acid ethyl ester (5.6 g, 36.4 mmol) was added to a solution of 4-methoxybenzyl amine (5 g, 36.4 mmol) in acetic acid (40 mL). The mixture was stirred for 10 min at rt. 4-Chloro-2-methylbenzaldehyde (6.77 g, 36.4 mmol) was added. The reaction mixture was heated to 120° C., stirred at this temperature overnight, allowed to cool to rt and diluted with acetonitrile. The resulting precipitate was collected by vacuum filtration and dried to provide 11 g of the title compound. tR: 1.80 min (LC-MS 2); ESI-MS: 414 [M+H]+ (LC-MS 2).

Workup

  1. temperatureThe reaction mixture was heated to 120° C.
  2. stirringstirred at this temperature overnight
  3. temperatureto cool to rt
  4. filtrationThe resulting precipitate was collected by vacuum filtration
  5. customdried

Sources & evidence

ORD record
ord-f570fc219c2449958107a0d39bcd8a5b
Source dataset
uspto-grants-2015_03
Patent number
US08969341B2

Reaction notes

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