Isatin → HCID 478641, compound

HRID 1756573Notes

Reaction equation

Cl[C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=O.[NH:14]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)C(=O)[C:15]1=O.F[C:26]1C=C2C(=CC=1)NC(=O)C2=O>>[CH3:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[C:10](=[O:12])[N:11]1[C:5]3[C:6](=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:7](=[O:9])[C:15]1=[N:14]2

Participants

Reactant 3

HCID 7054Isatin

HCID 784805-Chloroisatoic anhydride

HCID 2365665-Fluoroisatin

Product 1

HCID 478641HCID 478641, compoundYield 31%

Procedure

Using the procedure in Example 12 and substituting 6-methylisatoic anhydride for 5-chloroisatoic anhydride and isatin for 5-fluoroisatin gave the title compound in 31% yield: mp 304°-307° C.; 1H NMR (300 MHz, CDCl3) δ 8.65 (d, 1H), 7.9 (t, 1H), 7.9 (t, 1H), 7.88 (t, 1H), 7.78 (t, 1H), 7.68 (t, 1H), 7.42 (dt, 1H), 7.41 (t, 1H), 3.0 (s, 3H); MS (M+H)+ 263.1, (M+CH4CN)+ 304.

Sources & evidence

ORD record: ord-1db4e44090c04fc0b18eb0e4e8bee5da
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441955

Reaction notes

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