Hydrazine hydrate (1:1) → 9-phenyl-8-(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one

HRID 1967994Notes

Reaction equation

HRID 1967994 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12](OCC)=O)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:3]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH2:29].[NH2:30][NH2:31]>CO>[C:23]1([CH:3]2[C:2]3=[N:30][NH:31][C:12](=[O:29])[C:10]4[CH:9]=[CH:8][CH:7]=[C:6]([C:11]=43)[NH:5][CH:4]2[C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67260795Ethyl 4-oxo-3-phenyl-2-(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate

Product 1

HCID 1363851829-phenyl-8-(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-oneYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ethyl 4-oxo-3-phenyl-2-(pyridin-4-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (340 mg) in 85% hydrazine monohydrate (6 mL) and methanol (3 mL) was stirred at room temperature for 2 h. After the evaporation of the solvent, water was added. Filtered and washed the cake by water (5 mL) then ethyl acetate to obtain a white solid. The solid was dried in vacuum at 50° C. to obtain 9-phenyl-8-(pyridin-4-yl)-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (150 mg, yield: 48%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 4.38-4.40 (d, J=7.6 Hz, 1H), 4.84-7.86 (d, J=8.0 Hz, 1H), 7.15-7.25 (m, 6H), 7.30-7.31 (m, 2H), 7.39-7.41 (d, J=7.6 Hz, 1H), 7.51-7.52 (s, 1H), 7.59-7.62 (t, J=8.0 Hz, 1H), 8.43-8.44 (d, J=6.0 Hz, 2H) 12.19 (s, 1H); LC-MS (ESI) m/z: 341 (M+1)+.

Workup

  1. customAfter the evaporation of the solvent, water
  2. additionwas added
  3. filtrationFiltered
  4. washwashed the cake by water (5 mL)
  5. customethyl acetate to obtain a white solid
  6. customThe solid was dried in vacuum at 50° C.

Sources & evidence

ORD record
ord-d31c3857397042f0a1e3a9cd2ced868b
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

Loading…