HCID 10068965, compound → HCID 10066030, compound

HRID 2396056Notes

Reaction equation

CO[C:3](=[O:30])[C:4]1[C:5](=[CH:10][C:11]([N:22]([CH3:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:12]([N:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)C)[CH:13]=1)[C:6]([O:8]C)=O.COC(=O)C1C(=CC(N(C)C2C=CC=CC=2)=C([NH:44]C2C=CC=CC=2)C=1)C(OC)=O>>[CH3:29][N:22]([C:11]1[CH:10]=[C:5]2[C:6](=[O:8])[NH:44][C:3](=[O:30])[C:4]2=[CH:13][C:12]=1[NH:14][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 10068965HCID 10068965, compound

HCID 10431330HCID 10431330, compound

Product 1

HCID 10066030HCID 10066030, compound

Procedure

A solution of 564 mg (1.5 mmol) of 4,5-bis(anilino)phthalic acid dimethyl ester (Example 1b) in 5 ml of acetonitrile is heated at 80° C. for 16 hours with 0.93 ml (15 mmol) of methyl iodide and 442 mg (3.2 mmol) of anhydrous potassium carbonate in a bomb tube. The reaction mixture is concentrated to dryness by evaporation, the residue is twice digested in dichloromethane and filtered, and the filtrate is concentrated by evaporation. Repeated chromatography on silica gel with hexane/ethyl acetate yields the title compounds in the form of slightly yellowish powders. (A): FAB-MS: 405 [M+ +H]; (B): FAB-MS: 391 [M+ +H].

Sources & evidence

ORD record: ord-b086956880c3491bb3d7c77313d8b11f
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05491144

Reaction notes

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