Acetic Acid → Ethyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

HRID 557402Notes

Reaction equation

HRID 557402 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[C:8]2[C:3]=1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[O:7]2.[C:16]([CH:18]=[C:19]([O-])[CH3:20])#[N:17].[Na+].[NH2:23]/[C:24](/[CH3:31])=[CH:25]\[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(O)(=O)C>CC(O)C>[C:16]([C:18]1[CH:12]([C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:14])=[CH:5][C:4]3=[O:15])[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:24]([CH3:31])[NH:23][C:19]=1[CH3:20])#[N:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 574388885-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehydeHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 15979092Ethyl 5-cyano-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 100 mg (0.49 mmol) of 5-fluoro-2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 5 ml of 2-propanol is mixed with 50.96 mg (0.49 mmol) of sodium 1-cyanoprop-1-en-2-olate, 62.65 mg (0.49 mmol) of ethyl 3-aminocrotonate and 0.04 ml (0.73 mmol) of acetic acid and stirred under reflux for 3 h. After cooling, the mixture is concentrated. The residue is taken up in dichloromethane and washed with water. The organic phase is dried over sodium sulfate and concentrated. The resulting residue is crystallized from diethyl ether. The beige-colored crystals are filtered off with suction and dried at 40° C. in a vacuum drying oven. 120.7 mg (65.1% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. washwashed with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue is crystallized from diethyl ether
  8. filtrationThe beige-colored crystals are filtered off with suction
  9. customdried at 40° C. in a vacuum
  10. customdrying oven

Sources & evidence

ORD record
ord-4e30f5ffb4ce4981b48e72e20c3da914
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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