5-Methylisatin → HCID 478577, compound

HRID 1756570Notes

Reaction equation

Cl[C:2]1[CH:13]=[C:6]2[C:7](OC(=O)[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[CH3:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19](=O)[C:18]2=[O:25].FC1C=C2C(=CC=1)NC(=O)C2=O>>[CH3:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]1[C:19](=[N:11][C:5]3[C:6]([C:7]1=[O:8])=[CH:13][CH:2]=[CH:3][CH:4]=3)[C:18]2=[O:25]

Participants

Reactant 3

HCID 118405-Methylisatin

HCID 784805-Chloroisatoic anhydride

HCID 2365665-Fluoroisatin

Product 1

HCID 478577HCID 478577, compoundYield 36%

Procedure

Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 5-methylisatin for 5-fluoroisatin gave the title compound in 36% yield: mp 282.8°-284.8° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.28-8.38 (m, 2H) 7.94 (d, 2H) 7.64-7.78 (m, 3H) 3.34 (s, 3H); MS (M+H)+ 263.

Sources & evidence

ORD record: ord-29f778fe884242b0a0ce725849a792ae
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05441955

Reaction notes

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