Ethylenediamine → 9-Phenyl-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one

HRID 1730975Notes

Reaction equation

HRID 1730975 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([NH2:21])[CH2:19][NH2:20]>>[C:2]1([C:1]2[CH:16]=[CH:15][CH:14]=[C:10]3[C:9]=2[CH:17]2[NH:21][CH2:18][CH2:19][N:20]2[C:11]3=[O:13])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 68132-Benzoylbenzoic Acid

Product 1

HCID 214945869-Phenyl-1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-one

Procedure

Reflux 45 g. of o-benzoylbenzoic acid and 120 ml. of ethylenediamine for 3 hours. Pour the mixture into ice water, allow to stand until the mixture is at room temperature and separate the product by filtration. Recrystallize from ethanol to obtain 9-phenyl-1,2,3,9b-tetrahydro-5H-imidazo-[2,1-a]isoindol-5-one, m.p. 155°-7° C. Elemental analysis confirms the empirical formula C16H14N2O.

Workup

  1. temperatureReflux 45 g
  2. customis at room temperature
  3. customseparate the product
  4. filtrationby filtration
  5. customRecrystallize from ethanol

Sources & evidence

ORD record
ord-06aa031440834019bcb830f0cb77c577
Source dataset
uspto-grants-1976_11
Patent number
US03994920

Reaction notes

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