Hydrochloric Acid → HCID 12344327, compound

HRID 1706638Notes

Reaction equation

HRID 1706638 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[NH:5][C:6](=[O:16])[C:7]1[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:9](O)=O)#[N:2].C(OC(=O)C)(=[O:23])C.[OH-].[K+].OO.Cl>>[CH:17]1[C:4]2[N:5]3[C:6](=[O:16])[C:7]4[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=4[C:9]3=[N:2][C:1](=[O:23])[C:3]=2[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 837713HCID 837713, compound

Product 1

HCID 12344327HCID 12344327, compound

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.

Workup

  1. temperaturecooled

Sources & evidence

ORD record
ord-3b00487e7c2c48f2aaee5c8d72a833fd
Source dataset
uspto-grants-1980_06
Patent number
US04208343

Reaction notes

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