Acetic Acid → 4-(4-Cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile

HRID 1951402Notes

Reaction equation

HRID 1951402 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][C:4]=1[O:11][CH3:12])=O.[C:13]([CH:15]=[C:16]([O-])[CH3:17])#[N:14].[Na+].[NH2:20][C:21]1[CH:26]=[C:25]([CH3:27])[NH:24][C:23](=[O:28])[CH:22]=1.C(O)(=O)C>CC(O)C>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH:1]2[C:22]3[C:23](=[O:28])[NH:24][C:25]([CH3:27])=[CH:26][C:21]=3[NH:20][C:16]([CH3:17])=[C:15]2[C:13]#[N:14])=[C:4]([O:11][CH3:12])[CH:5]=1)#[N:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 100575014-Amino-2-hydroxy-6-methylpyridineHCID 166592514-Formyl-3-methoxybenzonitrileHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

Product 1

HCID 674174494-(4-Cyano-2-methoxyphenyl)-2,7-dimethyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

908 mg (5.64 mmol) of 4-formyl-3-methoxybenzonitrile are dissolved with 592 mg (5.64 mmol) of sodium 1-cyanoprop-1-en-2-olate, 700 mg (5.64 mmol) of 4-amino-6-methylpyridin-2(1H)-one [Bisagni, E., Hung, N. C., Synthesis, 765-766 (1984)] and 484 μl (8.46 mmol) of acetic acid in 30 ml of 2-propanol and heated at the reflux temperature under argon for 12 h. After cooling, the reaction mixture is filtered and the remaining solid is washed with diethyl ether (20 ml). 1798 mg (96% of theory) of the title compound are obtained as a white solid.

Workup

  1. temperatureheated at the reflux temperature under argon for 12 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. washthe remaining solid is washed with diethyl ether (20 ml)

Sources & evidence

ORD record
ord-c793c70348dd4bbb8278c6d80d40a8d4
Source dataset
uspto-grants-2013_03
Patent number
US08404709B2

Reaction notes

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