HCID 10068965, compound → HCID 10066030, compound

HRID 1376772Notes

Reaction equation

HRID 1376772 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

3

Reactant 2

HCID 10068965HCID 10068965, compoundHCID 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 1) 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-8b1453e955544220b6b58e127a35fc65
Source dataset
uspto-grants-1997_09
Patent number
US05663336

Reaction notes

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