P-Anisidine → 1-(4-Methoxyphenyl)-2-oxo-3-pyrrolidinecarboxylic acid

HRID 58561

Reaction equation

HRID 58561 reaction equation
CC1(C)[O:9][C:8](=[O:10])[C:5]2([CH2:7][CH2:6]2)[C:4](=[O:11])O1.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1>C(O)C>[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([N:19]2[CH2:6][CH2:7][CH:5]([C:8]([OH:9])=[O:10])[C:4]2=[O:11])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 33731171-(4-Methoxyphenyl)-2-oxo-3-pyrrolidinecarboxylic acidYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (0.500 g; 2.94 mmol) and 4-methoxyaniline (1.09 g; 8.82 mmol) in ethanol (3 mL) was irradiated in a microwave oven for 3 minutes at 100° C. The mixture was concentrated under reduced pressure and the residue was dissolved in a solution of sodium hydroxide 6N, washed with dichloromethane, acidified with a solution of hydrochloric acid 6N to pH=2, extracted with ethyl acetate dried and concentrated under reduced pressure to yield 0.11 g (16%) of a pale pink solid, which was used in the next step without further purification.

Workup

  1. customwas irradiated in a microwave oven for 3 minutes at 100° C
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in a solution of sodium hydroxide 6N
  4. washwashed with dichloromethane
  5. extractionextracted with ethyl acetate
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-396ad0628567443fa58f365338ee7392
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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