Isatin → HCID 478642, compound

HRID 1756574Notes

Reaction equation

HRID 1756574 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:17](=O)[C:15]1=O.FC1C=C2C(=CC=1)NC(=O)C2=O>>[CH3:17][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:24]=1[N:14]=[C:15]1[C:7](=[O:9])[C:6]3[C:5]([N:11]1[C:10]2=[O:12])=[CH:4][CH:3]=[CH:2][CH:13]=3

Participants

4

Reactant 3

HCID 7054IsatinHCID 784805-Chloroisatoic anhydrideHCID 2365665-Fluoroisatin

Product 1

HCID 478642HCID 478642, compoundYield 31%

Procedure

Using the procedure in Example 12 and substituting 3-methylisatoic anhydride for 5-chloroisatoic anhydride and isatin for 5-fluoroisatin gave the title compound in 31% yield: mp 247°-248° C.; 1H NMR (300 MHz, CDCl3) δ 8.64 (d, 1H), 8.28 (d, 1H), 7.92 (d, 1H), 7.78 (dt, 1H), 7.70 (d, 1H), 7.55 (t, 1H), 7.43 (dt, 1H), 275 (s, 1H); MS (M+H)+ 263, (M+CH4CN)+ 304.

Sources & evidence

ORD record
ord-c94f767ca14e4ffc8888e0efca5b082a
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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