Phthalic Anhydride → HCID 837713, compound

HRID 1706637Notes

Reaction equation

HRID 1706637 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12](#[N:20])[C:13]1[C:14](=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH2:15]>C(OCC)(=O)C>[C:12]([C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][C:4](=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:1]([OH:6])=[O:11])#[N:20]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 729132-Aminobenzonitrile

Product 1

HCID 837713HCID 837713, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of sublimed phthalic anhydride in ethyl acetate is reacted with a solution of anthranilonitrile in ethyl acetate to form 2'-cyanophthalanilic acid. The 2'-cyanophthalanilic acid is then boiled with acetic anhydride to convert the acid to 2'-cyanophthalanil. The 2'-cyanophthalanil is thereafter boiled in a mixture containing 2% potassium hydroxide and 2.4% hydrogen peroxide, cooled and neutralized with hydrochloric acid to cyclicize it and form isoindolo [2,1-a]quinazoline-5,11-dione. A similar procedure is set forth by Bogert and Hand, 24 J. Am. Chem. Soc., 1031 (1902) for preparing 2-methyl-4-ketodihydroquinazoline from N-acetylanthranilonitrile.

Sources & evidence

ORD record
ord-5f894d193f5b4e8faaaff47af8cb1bd0
Source dataset
uspto-grants-1980_06
Patent number
US04208343

Reaction notes

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