Acetic Acid → 5-Chloro-6-methoxy-2,3-dihydrospiro[indene-1,3'-pyrrolidine]-2',5'-dione

HRID 1661057Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7]([CH2:15][C:16]#[N:17])([C:13]#N)[CH2:6][CH2:5]2.[OH2:18].CC(O)=[O:21]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7]1([CH2:15][C:16](=[O:18])[NH:17][C:13]1=[O:21])[CH2:6][CH2:5]2

Participants

Conditions

Temperature: 200 °C

Procedure

To a solution of 5-chloro-1-(cyanomethyl)-6-methoxy-2,3-dihydro-1H-indene-1-carbonitrile (Prep17, 520 mg, 2.11 mmol) in AcOH (5.2 ml), H2SO4 (0.364 ml) was added. The mixture was stirred for 15 min at 200° C. Water was added and the mixture extracted with EA twice, solvent was evaporated, dried over Na2SO4, concentrated to give the title compound that was used in the next step without further purification. (540 mg, y=96%).

Workup

extractionthe mixture extracted with EA twice
customsolvent was evaporated
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-f5f06d476696481f9c04a317d8e48c82
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030322B2

Reaction notes

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