Hydrazine hydrate (1:1) → HCID 136186300, compound

HRID 1967885Notes

Reaction equation

HRID 1967885 reaction equation
O=[C:2]1[C:11]2[C:10]([C:12](OC)=O)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:3]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH2:28].[NH2:29][NH2:30]>O>[C:16]1([CH:4]2[NH:5][C:6]3[C:11]4[C:2](=[N:29][NH:30][C:12](=[O:28])[C:10]=4[CH:9]=[CH:8][CH:7]=3)[CH:3]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67258928HCID 67258928, compound

Product 1

HCID 136186300HCID 136186300, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-oxo-2,3-diphenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (100 mg, mmol) in hydrazine monohydrate (25 mL) was heated to reflux for 20 hr. The mixture was diluted with water (30 mL), extracted with ethyl acetate (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product. The crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 8:1) to give 8,9-diphenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one (15.6 mg, yield 16%) as a white solid. MS (ESI) m/z: 340 (M+1)+. 1H-NMR (400 MHz, CDCl3) δ 4.22-4.25 (d, J=9.6 Hz, 1H), 4.66-4.69 (d, J=9.6 Hz, 1H), 7.02-7.06 (m, 3H), 7.16-7.26 (m, 8H), 7.57-7.61 (t, J=7.8 Hz, 1H), 7.74-7.76 (d, J=7.6 Hz, 1H), 9.82 (s, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 hr
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customto give crude product
  8. customThe crude product was purified by chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 8:1)

Sources & evidence

ORD record
ord-a6ba4ffecb64446384f14fa887c8b219
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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