Acetic Anhydride → HCID 59299958, compound

HRID 2236457Notes

Reaction equation

[CH3:1][N:2]1[C:11](=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:13].C[C:15]([O:17][C:18](C)=O)=O.C(OC)(OC)OC>CN(C)C=O>[CH3:1][N:2]1[C:11](=[O:12])/[C:10](=[CH:15]/[O:17][CH3:18])/[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:13]

Participants

Conditions

Temperature: 125 °C

Procedure

To a stirred mixture of 0.35 g (2.0 mmol) of (N-methyl)isoquinoline-1,3(2H,4H)-dione, 3.2 ml of Ac2O, and 0.80 ml of N,N-dimethylformamide is added 0.44 ml (4.0 mmol) of (MeO)3CH at 25° C. The mixture is stirred at 125° C. for 30 m, cooled, and concentrated under high vacuum. The residue is recrystallized from Et2O-hexane to give 0.20 g of tan solid, mp 145-150° C. (dec); MS (ES+) m/z 218.2 (M+H)+1: Analysis for C12H11NO3: Calcd: C, 66.35; H, 5.10; N, 6.45. Found: C, 65.98; H, 4.99; N, 6.42.

Workup

temperaturecooled
concentrationconcentrated under high vacuum
customThe residue is recrystallized from Et2O-hexane

Sources & evidence

ORD record: ord-5d78a1618e1f4b6081891a49d0d1f3aa
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713994B2

Reaction notes

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