3-Nitrophthalic anhydride → HCID 792946, compound

HRID 1058077Notes

Reaction equation

[N+:1]([C:4]1[CH:14]=[CH:13][CH:12]=[C:6]2[C:7]([O:9][C:10](=[O:11])[C:5]=12)=O)([O-:3])=[O:2].[CH3:15][C@H:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)(Cl)Cl>[C:17]1([C@@H:16]([N:23]2[C:10](=[O:11])[C:5]3[C:6](=[CH:12][CH:13]=[CH:14][C:4]=3[N+:1]([O-:3])=[O:2])[C:7]2=[O:9])[CH3:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 180 °C

Procedure

386 mg of 3-nitrophthalic anhydride and 242 mg of (S)-α-methylbenzylamine were charged in an egg-plant type flask of 50 ml, followed by stirring under heating at a temperature of 180° C. for 1.5 hours. After cooled, the reaction product was dissolved in chloroform, purified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v), recrystallized from a mixed solvent of n-hexane-ethyl acetate, to obtain 443 mg of the desired product as a light yellow powder. Yield: 75%. m.p. 115-117° C.; MS(EI+) 296(M) Representative examples of the compounds of the present invention synthesized based on the Synthesis Examples or the methods for producing the compounds of the present invention as mentioned above, are listed in Table 1.

Workup

temperatureAfter cooled
custompurified by silica gel column chromatography (eluent; methylene chloride:methanol=30:1 v/v)
customrecrystallized from a mixed solvent of n-hexane-ethyl acetate

Sources & evidence

ORD record: ord-b71085e835934ab989eec60c897f8fd5
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515129B1

Reaction notes

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