Hydrazine hydrate (1:1) → HCID 136385220, compound

HRID 907770Notes

Reaction equation

HRID 907770 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12](OC)=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1.O=C1C2C(C(OCC)=O)=CC=CC=2NC(C2C=CC=CN=2)C1C1C=CC=CN=1.O.[NH2:57][NH2:58]>>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:4]1[NH:5][C:6]2[C:11]3[C:2](=[N:57][NH:58][C:12](=[O:13])[C:10]=3[CH:9]=[CH:8][CH:7]=2)[CH:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 67258285HCID 67258285, compoundHCID 67258925HCID 67258925, compound

Product 1

HCID 136385220HCID 136385220, compoundYield 37%

Procedure

A mixture of methyl 4-oxo-2,3-di(pyridin-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate and ethyl 4-oxo-2,3-di(pyridin-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (68 mg, 0.19 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-2-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (24 mg, yield 37%) as a light yellow solid. 1H-NMR (400 MHz, DMSO) δ 5.42-5.43 (d, J=5.2 Hz, 1H), 5.56-5.57 (d, J=5.2 Hz, 1H), 7.30-7.32 (d, J=8.0 Hz, 1H), 7.37-7.39 (d, J=8.0 Hz, 1H), 7.63-7.66 (t, J=6.6 Hz, 1H), 7.68-7.70 (m, 2H), 7.78-7.80 (d, J=7.2 Hz, 1H), 7.87-7.89 (d, J=8.0 Hz, 1H), 8.11-8.16 (m, 2H), 8.66-8.67 (d, J=4.8 Hz, 1H), 8.74-8.76 (d, J=5.6 Hz, 1H); 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-3854501583ac4ebd92725513b321f4a8
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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