Hydrazine hydrate (1:1) → HCID 136344732, compound

HRID 1467558Notes

Reaction equation

C(OC(OCC)C1C=C(C2C(C3C=CC=CC=3)C(=O)C3C(C(OC)=O)=CC=CC=3N2)C=CC=1)C.[CH2:35]([O:37][CH:38]([O:67][CH2:68][CH3:69])[C:39]1[CH:40]=[C:41]([CH:45]2[CH:54]([C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)[C:53](=O)[C:52]3[C:51]([C:62]([O:64]CC)=O)=[CH:50][CH:49]=[CH:48][C:47]=3[NH:46]2)[CH:42]=[CH:43][CH:44]=1)[CH3:36].O.[NH2:71][NH2:72]>CO>[CH2:68]([O:67][CH:38]([O:37][CH2:35][CH3:36])[C:39]1[CH:40]=[C:41]([CH:45]2[NH:46][C:47]3[C:52]4[C:53](=[N:71][NH:72][C:62](=[O:64])[C:51]=4[CH:50]=[CH:49][CH:48]=3)[CH:54]2[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH:42]=[CH:43][CH:44]=1)[CH3:69]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl 2-(3-(diethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 2-(3-(diethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (160 mg, 0.36 mmol) in 85% hydrazine monohydrate (4 mL) and methanol (3 mL) was stirred at 25° C. for overnight. The mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give the 8-(3-(diethoxymethyl)phenyl)-9-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (90 mg, yield 58%) as a yellow solid. LC-MS (ESI) m/z: 442 (M+1)+.

Workup

extractionThe mixture was extracted with ethyl acetate (50 mL×3)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-9170efe634524e1aa71660df60dc0fa3
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999987B2

Reaction notes

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