3-Hydroxy-4-methoxy-2-nitrobenzoic acid → HCID 86628081, compound

HRID 1401283Notes

Reaction equation

[OH:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=O.[Cl:16][C:17]1[N:26]=[C:25]([CH3:27])[C:24]([Cl:28])=[C:23]([CH3:29])[C:18]=1/[C:19](=[N:21]/O)/[NH2:20]>CN(C)C(=O)C>[Cl:16][C:17]1[C:18]([C:19]2[N:20]=[C:5]([C:4]3[C:3]([N+:13]([O-:15])=[O:14])=[C:2]([OH:1])[C:10]([O:11][CH3:12])=[CH:9][CH:8]=3)[O:7][N:21]=2)=[C:23]([CH3:29])[C:24]([Cl:28])=[C:25]([CH3:27])[N:26]=1

Participants

Conditions

Temperature: 135 °C

Procedure

To a stirred suspension of 3-hydroxy-4-methoxy-2-nitrobenzoic acid (0.900 g, 4.22 mmol) in N,N-dimethylacetamide (10.35 mL) at room temperature was added 1,1-carbonyldiimidazole (1.540 g, 9.506 mmol) in 7.65 ml of N,N-dimethylacetamide dropwise. After stirring for three hours, (Z)-2,5-dichloro-N′-hydroxy-4,6-dimethylnicotinimidamide (1.19 g, 5.107 mmol) was added in 2.7 ml of N,N-dimethylacetamide in one portion. The resulting mixture was stirred for one hour and forty five minutes then heated at 135° C. for one hour. The reaction mixture was poured onto ice/2N HCl mixture. The precipitate was filtered off, washed with water and dried under vacuum to give a yellow solid. Recrystallisation from dichloromethane/isopropanol gave 3-(3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-1,2,4-oxadiazol-5-yl)-6-methoxy-2-nitrophenol as a yellow solid (0.317 g, 18%).

Workup

stirringThe resulting mixture was stirred for one hour and forty five minutes
additionThe reaction mixture was poured onto ice/2N HCl mixture
filtrationThe precipitate was filtered off
washwashed with water
customdried under vacuum
customto give a yellow solid
customRecrystallisation from dichloromethane/isopropanol

Sources & evidence

ORD record: ord-64b8af5a9e994ee1ae9f36b989847277
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907099B2

Reaction notes

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