2-[(2,3-dihydro-1H-inden-2-ylamino)carbonyl]benzoic acid → 2-(1,3-Isoindolinedion-2-yl)indane

HRID 57169Notes

Reaction equation

[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11](=[O:21])[C:12]1[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:14]([OH:16])=O>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[CH2:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:1][CH:2]1[N:10]1[C:14](=[O:16])[C:13]2[C:12](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]1=[O:21]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of compound 747-B (1.8 g, 0.74 mmol) in DMF (20 mL) was added DMAP (0.782 g; 0.74 mmol) and the reaction mixture was heated at 120° C. for 18 h. The reaction mixture was cooled, diluted with H2O, and the precipitate filtered and dried under vacuo to afford 1.2 g of compound 747-C as a light brown solid. 1H-NMR (CDCl3) δ 3.18 (dd, 2H), 3.63 (dd, 2H), 5.16 (q, 1H), 7.14-7.24 (m, 4H), 7.68-7.77 (m, 2H), 7.79-7.90 (m, 2H); MS: m/z 264.1 (MH+).

Workup

temperatureThe reaction mixture was cooled
filtrationthe precipitate filtered
customdried under vacuo

Sources & evidence

ORD record: ord-3317fbc928274573891691b7d67c227f
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434711B2

Reaction notes

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