Hydrazine hydrate (1:1) → HCID 136053647, compound

HRID 907773Notes

Reaction equation

HRID 907773 reaction equation
[CH:1]([CH:4]1[C:13](=O)[C:12]2[C:11]([C:15](OC)=[O:16])=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6][CH:5]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:3])[CH3:2].O.[NH2:26][NH2:27]>>[CH:1]([CH:4]1[C:13]2=[N:26][NH:27][C:15](=[O:16])[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([C:12]=32)[NH:6][CH:5]1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67258953HCID 67258953, compound

Product 1

HCID 136053647HCID 136053647, compoundYield 15%

Conditions

Temperature
40 °C

Procedure

Methyl 3-isopropyl-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (35 mg, 1 mmol) and hydrazine monohydrate (20 mL) were added and the mixture was stirred under 40° C. for 3 h. The resulting mixture was extracted with ethyl acetate (100 mL×4) and concentrated, purified with prep-HPLC. 7 mg of solid 9-isopropyl-8-phenyl-8,9-dihydro-2H-pyrido[4,3,2-de]phthalazin-3(7H)-one was obtained (yield: 15%). 1H-NMR (400 MHz, DMSO-d6): δ 0.82-0.83 (d, J=5.2 Hz, 3H), 1.15-1.17 (d, J=5.2 Hz, 3H), 1.89-1.93 (m, 1H), 2.71-2.73 (d, J=6.0 Hz, 1H), 4.83 (s, 1H), 7.11-7.26 (m, 7H), 7.51-7.54 (m, 2H), 12.11 (s, 1H). LC-MS (ESI) m/z: 306 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (100 mL×4)
  2. concentrationconcentrated
  3. custompurified with prep-HPLC

Sources & evidence

ORD record
ord-e3dff486ac0341598e6ef41f946ef7d3
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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