Hydrogen Peroxide → 2-Methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

HRID 1289219Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[C:14]#[N:15])[CH2:10][CH2:9][CH2:8]2)(=O)[CH3:2].[OH:16]O.[OH-].[Na+].O>C(O)C>[CH3:2][C:1]1[NH:15][C:14](=[O:16])[C:13]2[C:5](=[CH:6][C:7]3[CH2:8][CH2:9][CH2:10][C:11]=3[CH:12]=2)[N:4]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 5-acetamido-6-cyanoindan (104 g), hydrogen peroxide (30% solution in water, 400 ml), sodium hydroxide (35 g), water (200 ml) and ethanol (1 L) was stirred and heated to 50° C. for 1 hour. The mixture was cooled to ambient temperature and evaporated. The residue was dissolved in water (2 L) and the solution was acidified to pH 5 by the addition of 2N aqueous hydrochloric acid. The precipitate was isolated, washed with water and dried under vacuum. There was thus obtained 2-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (100 g), m.p. 284° C.

Workup

temperatureThe mixture was cooled to ambient temperature
customevaporated
dissolutionThe residue was dissolved in water (2 L)
additionthe solution was acidified to pH 5 by the addition of 2N aqueous hydrochloric acid
customThe precipitate was isolated
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-23224da71deb4288af55c192493762eb
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747499

Reaction notes

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