1,2-Dimethylhydrazine → 3-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinoline

HRID 720430

Reaction equation

HRID 720430 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20](F)=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2].CNNC.[CH3:29][N:30](C=O)[CH3:31]>O>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([N:30]([CH3:31])[CH3:29])=[CH:19][CH:18]=2)[N:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][C:7]=12)#[N:2]

Participants

5

Reactant 3

HCID 13221,2-DimethylhydrazineHCID 6228DimethylformamideHCID 102676303-Cyano (4-fluoro-benzoyl)-pyrrolo[1,2-a]quinoline

Product 1

HCID 218921233-Cyano-1-(4-dimethylamino-benzoyl)-pyrrolo[1,2-a]quinolineYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-cyano-1-[4-fluoro-benzoyl]-pyrrolo[1,2-a]quinoline (56 mg, 0.18 mmol) and dimethylhydrazine (118 mg, 1.96 mmol) in DMF (5 mL) was refluxed for 24 h. It was diluted with water (50 mL) and extracted with EtOAc (3×20 mL). The combined organic layers were dried, concentrated and the residue was purified by column chromatography (EtOAc/Hexane 6:1) to give 15 mg (25%) of the title compound. 1H NMR (CDCl3): 8.11–8.05–7.95 (m, 3H), 7.82–7.78 (m, 2H), 7.63–7.42 (m, 4H), 7.31 (s, 1H), 6.75 (d, J=9.30 Hz, 2H), 3.14 (s, 6H). MS, 340 (M+1).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customthe residue was purified by column chromatography (EtOAc/Hexane 6:1)

Sources & evidence

ORD record
ord-5009080523824638a9d9dbb27028aedd
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Linked notes

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