Isatin → HCID 336271, compound

HRID 1756565Notes

Reaction equation

HRID 1756565 reaction equation
[N+:1]([C:4]1[CH:15]=[C:8]2[C:9]([O:11][C:12](=O)[NH:13][C:7]2=[CH:6][CH:5]=1)=O)([O-:3])=[O:2].Cl[C:17]1[CH:28]=[C:21]2[C:22](OC(=O)[NH:26][C:20]2=[CH:19][CH:18]=1)=[O:23].N1C2C(=CC=CC=2)C(=O)C1=O.FC1C=C2C(=CC=1)NC(=O)C2=O>CN(C=O)C>[N+:1]([C:4]1[CH:15]=[C:8]2[C:7](=[CH:6][CH:5]=1)[N:13]=[C:12]1[C:22](=[O:23])[C:21]3[C:20]([N:26]1[C:9]2=[O:11])=[CH:19][CH:18]=[CH:17][CH:28]=3)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 7054IsatinHCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-HCID 784805-Chloroisatoic anhydrideHCID 2365665-Fluoroisatin

Product 1

HCID 336271HCID 336271, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using the procedure in Example 12, and substituting NMP for DMF, 5-nitroisatoic anhydride for 5-chloroisatoic anhydride and isatin for 5-fluoroisatin gave 495 mg (24%) of the title compound: mp 349° C. (dec); 1H NMR(CDCl3)δ 7.46-7.54 (m, 1H), 7.84-8.00 (m, 3H), 8.18-8.22 (m, 1H), 8.62-8.68 (m, 2H).

Sources & evidence

ORD record
ord-49b1fedd37ac49a59624bebf2a708c17
Source dataset
uspto-grants-1995_08
Patent number
US05441955

Reaction notes

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