4-Nitrophthalic acid anhydride → HCID 86660587, compound

HRID 718726Notes

Reaction equation

Cl.[NH2:2][C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10].[N+:26]([C:29]1[CH:30]=[C:31]2[C:36](=O)[O:35][C:33](=[O:34])[C:32]2=[CH:38][CH:39]=1)([O-:28])=[O:27].C([O-])(=O)C.[Na+]>C(O)(=O)C>[N+:26]([C:29]1[CH:30]=[C:31]2[C:32](=[CH:38][CH:39]=1)[C:33](=[O:34])[N:2]([C:3]1([CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:8][CH2:7][C:6](=[O:9])[NH:5][C:4]1=[O:10])[C:36]2=[O:35])([O-:28])=[O:27]

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of 4 (0.4 g, 1.08 mmol), 4-nitrophthalic anhydride (0.259 g, 1.34 mmol), and sodium acetate (0.125 g, 1.45 mmol) was added acetic acid (4 mL) and the resulting mixture was stirred at 130° C. After 6 h, the mixture was quenched with sodium bicarbonate and extracted with DCM. The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography (95:5 DCM:MeOH) afforded 9 (0.45 g, 87%). Rf=0.36 (95:5 DCM:MeOH). 1H NMR (400 MHz, CDCl3) δ 8.62 (par obsc s, 1H), 8.60-8.51 (par obsc m, 1H), 8.16-7.86 (m, 2H), 7.44-7.27 (m, 5H), 5.07 (m, 2H), 3.23 (m, 3H), 2.93-2.49 (m, 3H), 2.46-2.23 (m, 1H), 2.14 (m, 1H), 1.79-1.47 (m, 3H), 1.45-1.17 (m, 2H), 1.00-0.75 (m, 1H). MS (ESI) m/z calcd for C25H25N4O8 [M+H]+ 509.5, found 509.3.

Workup

customthe mixture was quenched with sodium bicarbonate
extractionextracted with DCM
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customPurification by flash chromatography (95:5 DCM:MeOH)

Sources & evidence

ORD record: ord-660271345ebd480ab709fda8a2b14cc7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193989B2

Reaction notes

Loading…