Hydrazine hydrate (1:1) → HCID 136374685, compound

HRID 907887Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:39][CH2:40][CH3:41])[C:5]1[CH:6]=[C:7]([CH:11]2[CH:20]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[CH:22]=3)[C:19](=O)[C:18]3[C:17]([C:35](OC)=[O:36])=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12]2)[CH:8]=[CH:9][CH:10]=1)[CH3:2].C(OC(OCC)C1C=C(C2C(C3C=CC=C(C(OCC)OCC)C=3)C(=O)C3C(C(OCC)=O)=CC=CC=3N2)C=CC=1)C.O.[NH2:85][NH2:86]>CO>[CH2:40]([O:39][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:6]=[C:7]([CH:11]2[NH:12][C:13]3[C:18]4[C:19](=[N:85][NH:86][C:35](=[O:36])[C:17]=4[CH:16]=[CH:15][CH:14]=3)[CH:20]2[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33])[CH:22]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:41]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 2,3-bis(3-(diethoxymethyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 2,3-bis(3-(diethoxymethyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (370 mg, 0.59 mmol) in hydrazine monohydrate (5 mL) and methanol (5 mL) was stirred at 50° C. for 2 hr. The mixture was cooled to room temperature and filtered to give 8,9-bis(3-(diethoxymethyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (250 mg, yield 77%) as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.99-1.08 (m, 12H), 3.27-3.33 (m, 8H), 4.28-4.31 (d, J=8.8 Hz, 1H), 4.74-4.76 (d, J=8.4 Hz, 1H), 5.31-5.32 (d, J=6.8 Hz, 2H), 7.04 (s, 1H), 7.12-7.26 (m, 7H), 7.31-7.43 (m, 3H), 7.56-7.60 (t, J=8.0 Hz, 1H); LC-MS (ESI) m/z: 544(M+1)+.

Workup

temperatureThe mixture was cooled to room temperature
filtrationfiltered

Sources & evidence

ORD record: ord-0cdba2dfa6df451baffc2e11e043c046
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012976B2

Reaction notes

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