Potassium Carbonate → HCID 22055255, compound

HRID 1829922Notes

Reaction equation

HRID 1829922 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].Cl.Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1.C([O-])([O-])=O.[K+].[K+].CC(N(C)C)=O>CC#N.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 31374DimethylacetamideHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 22055255HCID 22055255, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-chloro-4-nitro-phenol (202 mg, 1.16 mmol), 2-chloromethyl-quinoline hydrochloride (224 mg, 1.04 mmol), K2CO3 (354 mg, 2.55 mmol) in CH3CN (3.6 ml) was heated at 70° C. for 8 h. DMA (2 ml) was added, and the mixture was heated at 80° C. for 4 h. The mixture was cooled to rt, diluted with EtOAc (120 ml), washed with H2O (6×80 ml) and brine (1×80 ml), dried (MgSO4) and filtered. The filtrate was concentrated to give 12A (280 mg, 85%).

Workup

  1. temperaturethe mixture was heated at 80° C. for 4 h
  2. temperatureThe mixture was cooled to rt
  3. washwashed with H2O (6×80 ml) and brine (1×80 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-87425b2cf56b4138b4daae92aab90b90
Source dataset
uspto-grants-2006_06
Patent number
US07064203B2

Reaction notes

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