4-Aminophenol → Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate

HRID 1993393Notes

Reaction equation

HRID 1993393 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11](=[O:19])[C:12](=[CH2:18])[CH2:13][C:14](OC)=[O:15]>CCOC(C)=O>[CH3:9][O:10][C:11]([CH:12]1[CH2:13][C:14](=[O:15])[N:1]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH2:18]1)=[O:19]

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 69240Dimethyl itaconate

Product 1

HCID 2883518Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-amino-phenol (3 g, 0.027 mol) and 2-methylene-succinic acid dimethyl ester (4.35 g, 0.027 mol) was heated to 110° C. for 16 h. The dark brown glass was dissolved in EtOAc and purified by silica gel chromatography (20% EtOAc/hexane to EtOAc) to give an orange oil. MS (ESI pos. ion) m/z: 236.2 (M+H). Calc'd Exact Mass for C12H13NO4: 235.24.

Workup

  1. custompurified by silica gel chromatography (20% EtOAc/hexane to EtOAc)
  2. customto give an orange oil

Sources & evidence

ORD record
ord-b597c88e968248d7a1103a0ad0a67c04
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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