Water → 6-Methoxy-4-phenyl-2H-phthalazin-1-one

HRID 2297407Notes

Reaction equation

CC1(C)C[O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)=[N:3]1.O.[NH2:25]N.O.C([O-])(O)=O.[Na+]>Cl.C(O)(=O)C>[CH3:14][O:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[C:4](=[O:5])[NH:3][N:25]=[C:15]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of [2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-phenyl-methanone (34 g, 11 mmoles), prepared as described in example 12, in 3N HCl (45 ml) was refluxed under stirring for 2 days, then added with 36% HCl (10 ml). After 20 hours the mixture was cooled and extracted more times with CHCl3. The organic phases were anhydrified and brought to dryness. The residue was dissolved in acetic acid and treated with hydrazine monohydrate (0.96 g, 19.24 mmoles) in acetic acid (7 ml). The mixture was heated to 80° C. under dry N2 and stirring for 20 hours, then brought to small volume, poured into water, neutralised with NaHCO3 in excess and extracted with CHCl3. The organic phases anhydrified and brought to dryness yielded 0.6 g of the title compound (yield: 37%). m.p.: 230-235° C.

Workup

customprepared
temperaturewas refluxed
temperatureAfter 20 hours the mixture was cooled
extractionextracted more times with CHCl3
dissolutionThe residue was dissolved in acetic acid
stirringstirring for 20 hours
extractionextracted with CHCl3

Sources & evidence

ORD record: ord-fa89cae9447348de9bd6f2bd3db5c1b5
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492360B1

Reaction notes

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