Acetic Acid → Methyl 3-(6-phenyl-pyridin-2-yl)-benzoate

HRID 628845Notes

Reaction equation

CN(C)C=CC([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)=O.[C:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)C.[C:27]([O-])(=O)[CH3:28].[NH4+:31].[C:32](O)(=O)[CH3:33]>>[C:21]1([C:18]2[N:31]=[C:28]([C:16]3[CH:15]=[C:10]([CH:9]=[CH:8][CH:7]=3)[C:11]([O:13][CH3:14])=[O:12])[CH:27]=[CH:33][CH:32]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 7410Acetophenone

HCID 517165Ammonium Acetate

HCID 53416580Methyl 4-[3-(dimethylamino)acryloyl]benzoate

Product 1

HCID 69232498Methyl 3-(6-phenyl-pyridin-2-yl)-benzoate

Conditions

Temperature: 80 °C

Procedure

Part B. A solution of (methyl 4-(3-dimethylamino-acryloyl)-benzoate) (100 mg) in acetic acid (5 mL) is treated with acetophenone and ammonium acetate (77 mg). The resulting mixture is heated to 80° C. for 18 h, then cooled and evaporated under a stream of nitrogen. The resulting solid is recrystallized in ethyl acetate-hexane to afford methyl 3-(6-phenyl-pyridin-2-yl)-benzoate. MS (ES+): m/e 290.2 (100).

Workup

temperaturecooled
customevaporated under a stream of nitrogen
customThe resulting solid is recrystallized in ethyl acetate-hexane

Sources & evidence

ORD record: ord-1721f7f6a5c94bec9a2392bebe2f5c97
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315467B2

Reaction notes

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