Hydrazine hydrate (1:1) → HCID 136409115, compound

HRID 1467504Notes

Reaction equation

HRID 1467504 reaction equation
[CH2:1]([O:3][CH:4]([O:39][CH2:40][CH3:41])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH:20]([C:21]3[CH:26]=[CH:25][C:24]([CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:23][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:7][CH:6]=1)[CH3:2].C(OC(OCC)C1C=CC(C2C(C3C=CC(C(OCC)OCC)=CC=3)C(=O)C3C(C(OCC)=O)=CC=CC=3N2)=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:10]=[CH:9][C:8]([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][C:24]([CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[CH:23][CH:22]=2)=[CH:7][CH:6]=1)[CH3:41]

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67387237HCID 67387237, compoundHCID 67387522HCID 67387522, compound

Product 1

HCID 136409115HCID 136409115, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 2,3-bis(4-(diethoxymethyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 2,3-bis(4-(diethoxymethyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate (240 mg, 0.43 mmol) in hydrazine monohydrate (5 mL) and methanol (5 mL) was stirred at 40° C. for 2 hr. The mixture was cooled to room temperature and filtered to give the 8,9-bis(4-(diethoxymethyl)phenyl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (120 mg, yield 52%) as a light yellow solid. LC-MS (ESI) m/z: 544 (M+1)+. MS (ESI) m/e 381 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-d8ba32fae6a24983901ca9c27714162e
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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