3-Nitrophthalic anhydride → HCID 792946, compound

HRID 2301913Notes

Reaction equation

HRID 2301913 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

4

Reactant 2

HCID 216313-Nitrophthalic anhydrideHCID 758181-Phenethylamine, (-)-

Product 1

HCID 792946HCID 792946, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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)+

Workup

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

Sources & evidence

ORD record
ord-766401460d214fc8818c60f011cdc14d
Source dataset
uspto-grants-2002_08
Patent number
US06429212B1

Reaction notes

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