Potassium Carbonate → HCID 21892140, compound

HRID 720428Notes

Reaction equation

HRID 720428 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[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].Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[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 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 21892125HCID 21892125, compound

Product 1

HCID 21892140HCID 21892140, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-cyano-1-(3-hydroxy-benzoyl)-pyrrolo[1,2-a]quinoline (31.2 mg, 0.1 mmol), 4-(2-chloroethyl)morpholine hydrochloride (37.2 mg, 0.2 mmol), potassium carbonate (165 mg, 1 mmol) in acetone (5 mL) was refluxed for 4 h. It was evaporated to dryness and the residue was purified by column chromatography (EtOAc) to give 16 mg (37%) of the title compound. 1H NMR (CDCl3): 8.06 (d, J=8.7 Hz, 1H), 7.86–7.83 (m, 1H), 7.75–7.43 (m, 8H), 7.26–7.20 (m, 1H), 4.20 (t, J=5.60 Hz, 2H), 3.74 (t, J=4.80 Hz, 4H), 2.85 (t, J=5.40 Hz, 2H), 2.60 (t, (t, J=4.50 Hz, 4H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customIt was evaporated to dryness
  3. customthe residue was purified by column chromatography (EtOAc)

Sources & evidence

ORD record
ord-abeb41c07a904d0e91061670e3d515bb
Source dataset
uspto-grants-2006_11
Patent number
US07135480B2

Reaction notes

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