Methanol → HCID 18957374, compound

HRID 2379558Notes

Reaction equation

HRID 2379558 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][CH2:10][CH:9]2[C:14]([O:16]C)=[O:15])[CH:5]=[CH:6][CH:7]=1.O[Li].O.CO>O>[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](=[O:13])[CH2:11][CH2:10][CH:9]2[C:14]([OH:16])=[O:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 18957384HCID 18957384, compound

Product 1

HCID 18957374HCID 18957374, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 1-(3-hydroxyphenyl)-5-oxo-2-pyrrolidinecarboxylate (10.00 g, 42 mmol), LiOH.H2O (5.36 g, 128 mmol), MeOH (200 mL) and H2O (50 mL) was stirred at room temperature for about 1 hour. The MeOH was removed in vacuo and the residue diluted with H2O and 2N HCl solution to pH=1. The solid was filtered off, dried in air and suspended in hot CH3CN (200 mL). Filtration gave 1-(3-hydroxyphenyl)-5-oxo-2-pyrrolidinecarboxylic acid (8.06 g, 85%), mp 183-185° C. IR (KBr) 3600-2300 (OH), 1710 (CO2H), 1695 (CONH) cm-1. 1H NMR (DMSO-d6/CDCl3) δ2.05 to 2.15 (1H, m, pyrrolidine ring H), 2.30-2.50 (3H, m, pyrrolidine ring H), 4.58 (1H, dd, J=9 Hz, J'= 2 Hz, CHCO2H), 6.52 (1H, dd, J=8 Hz, J'=2 Hz, aromatic H), 6.81 (1H, dd, J=8 Hz, J'=2Hz, aromatic H), 7.02 to 7.08 (2H, m, aromatic H), 9.16 (1H, bs, OH); MS m/z 222 (MH+).

Workup

  1. customThe MeOH was removed in vacuo
  2. additionthe residue diluted with H2O and 2N HCl solution to pH=1
  3. filtrationThe solid was filtered off
  4. customdried in air
  5. filtrationFiltration

Sources & evidence

ORD record
ord-eb10cba37fe9421389f941dfe04bb364
Source dataset
uspto-grants-1994_11
Patent number
US05362879

Reaction notes

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