Hydrazine hydrate (1:1) → HCID 135924347, compound

HRID 1967886Notes

Reaction equation

HRID 1967886 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:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:3]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.O=C1C2C(C(OCC)=O)=CC=CC=2NC(C2C=CN=CC=2)C1C1C=CN=CC=1.O.[NH2:57][NH2:58]>>[N:19]1[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]=[CH:24][N:25]=[CH:26][CH:27]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67258454HCID 67258454, compoundHCID 67258718HCID 67258718, compound

Product 1

HCID 135924347HCID 135924347, compoundYield 68%

Procedure

A mixture of methyl 4-oxo-2,3-di(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 4-oxo-2,3-di(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (60 mg, 0.17 mmol) in hydrazine monohydrate (7 mL) was heated to reflux for 4 hr. Then the mixture was cooled to room temperature and solvent was removed in vacuum to give crude product. The crude product was purified by pre-HPLC to give 8,9-di(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (15 mg, yield 68%) as a light yellow solid. 1H-NMR (400 MHz, DMSO) δ 4.46-4.48 (d, J=8.4 Hz, 1H), 4.90-4.92 (d, J=8.4 Hz, 1H), 7.16-7.20 (m, 3H), 7.32-7.34 (d, J=5.2 Hz, 2H), 7.40-7.42 (d, J=8.4 Hz, 1H), 7.55 (s, 1H), 7.59-7.63 (t, J=8.0 Hz, 1H), 8.40-8.40 (d, J=5.2 Hz, 2H), 8.44-8.45 (d, J=5.2 Hz, 2H). LC-MS (ESI) m/z: 342 (M+1)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hr
  3. customsolvent was removed in vacuum
  4. customto give crude product
  5. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-a56fd72abba546f5b90f626a8bf0932f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

Loading…