Pyridine → HCID 178489011, compound

HRID 643862Notes

Reaction equation

[NH2:1][C:2]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].N1C=CC=CC=1.[CH3:20][O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.CCO.O>[CH3:13][O:12][C:9]1[C:10]([CH3:11])=[C:2]2[C:3]([C:4]([OH:5])=[N:6][C:26]([C:25]3[CH:29]=[CH:30][C:22]([O:21][CH3:20])=[CH:23][CH:24]=3)=[N:1]2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 5 °C

Procedure

To a suspension of 2-amino-4-methoxy-3-methyl benzamide in dry THF (60 ml) was added pyridine (2 eq) and the mixture was cooled to 5° C. 4-Methoxybenzoic acid chloride (1.25 eq) was added slowly and the mixture was stirred at room temperature overnight. The mixture was evaporated under reduced pressure and then suspended in water. The compound was left in the water for some hours, filtered and washed with cold water and diethyl ether and dried under vacuum. The residue was then added to a suspension of sodium carbonate (2.5 eq) in a 1:1 mixture of water and EtOH and the mixture was refluxed for two hours. The EtOH was removed under reduced pressure, a solution of 5% citric acid was added and the mixture was allowed to stay overnight. The title compound was isolated by filtration, then washed with water and diethyl ether and dried under vacuum. (5.5 g, 92%).

Workup

customThe mixture was evaporated under reduced pressure
waitThe compound was left in the water for some hours
filtrationfiltered
washwashed with cold water and diethyl ether
customdried under vacuum
temperaturethe mixture was refluxed for two hours
customThe EtOH was removed under reduced pressure
additiona solution of 5% citric acid was added
waitto stay overnight

Sources & evidence

ORD record: ord-e222cfa629204d4f841fa099f4b6f96f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700552B2

Reaction notes

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