Hydrazine hydrate (1:1) → HCID 136385312, compound

HRID 1967887Notes

Reaction equation

HRID 1967887 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12]([O:14]C)=O)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:3]1[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1.O=C1C2C(C(OCC)=O)=CC=CC=2NC(C2C=NC=CC=2)C1C1C=NC=CC=1.O.[NH2:57][NH2:58]>CO>[N:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:4]2[NH:5][C:6]3[C:11]4[C:2](=[N:57][NH:58][C:12](=[O:14])[C:10]=4[CH:9]=[CH:8][CH:7]=3)[CH:3]2[C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67259487HCID 67259487, compoundHCID 67260756HCID 67260756, compound

Product 1

HCID 136385312HCID 136385312, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-oxo-2,3-di(pyridin-3-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 4-oxo-2,3-di(pyridin-3-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (480 mg, 1.34 mmol) in hydrazine monohydrate (20 mL) and methanol (5 mL) was heated to reflux for 2 hr. The mixture was then cooled to room temperature and filtered to give 8,9-di(pyridin-3-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (320 mg, yield 68%) as a light yellow solid. 1H-NMR (400 MHz, DMSO-d6) δ 4.51-4.53 (d, J=8.4 Hz, 1H), 4.89-4.91 (d, J=8.4 Hz, 1H), 7.18-7.20 (m, 1H), 7.24-7.27 (m, 1H), 7.31-7.33 (m, 1H), 7.43-7.44 (m, 1H), 7.60 (s, 1H), 7.58-7.63 (m, 2H), 7.79-7.81 (m, 1H), 8.32-8.34 (m, 2H), 8.41-8.43 (m, 1H), 8.45-8.46 (d, J=1.6 Hz, 1H); LC-MS (ESI) m/z: 342 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. filtrationfiltered

Sources & evidence

ORD record
ord-d567362696cf491d922f1bae92d6735f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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