4-Aminobenzonitrile → 1-(4-Cyanophenyl)-2-oxopyrrolidine-3-carboxylic acid

HRID 58559

Reaction equation

HRID 58559 reaction equation
CC1(C)[O:9][C:8](=[O:10])[C:5]2([CH2:7][CH2:6]2)[C:4](=[O:11])O1.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=1>C(O)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([N:13]2[CH2:6][CH2:7][CH:5]([C:8]([OH:9])=[O:10])[C:4]2=[O:11])=[CH:15][CH:16]=1)#[N:19]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 668318301-(4-Cyanophenyl)-2-oxopyrrolidine-3-carboxylic acidYield 36%

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-aminobenzonitrile (1.04 g, 8.82 mmol) in ethanol (3 mL) was irradiated in a microwave oven for 3 minutes at 100° C. The solution 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 sodium hydrogen phosphate (1M) to pH=2, extracted with ethyl acetate dried and concentrated under reduced pressure to yield 0.240 g (36%) of a brown 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 solution 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-f7052addfd7b40a1801b391e36511771
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

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