O-Phenylenediamine → O-Phenylenediamine

HRID 1439175Notes

Reaction equation

HRID 1439175 reaction equation
[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:4])[CH2:2]C.[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20]>ClC1C=CC=CC=1>[CH3:2][C:1]12[NH:21][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:20]1[C:7](=[O:9])[C:6]1[C:5]2=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:1]([C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:4])[CH3:2].[C:14]1([NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20]

Participants

6

Reactant 2

HCID 7243O-PhenylenediamineHCID 753842-Propionylbenzoic acid

Product 3

HCID 7243O-PhenylenediamineHCID 684742-Acetylbenzoic acidHCID 3901704b-methyl-5H-isoindolo[2,1-a]benzimidazol-11-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

17.8 Parts of o-propionyl-benzoic acid and 11 parts of o-phenylenediamine are heated for 1 hour in 200 parts of chlorobenzene while distilling off water and chlorobenzene. The excess chlorobenzene is then removed in vacuo and the residue is distilled under high vacuum. The destillate solidifies and is recrystallised from a little ethyl acetate. The pure 4b-ethyl-4b,5-dihydro-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-one of the formula ##STR30## melts at 134°. 4b-methyl-4b,5-dihydro-11H-benzo[4,5]imidazo[2,1-a]isoindol-11-one (M.P. 182.5°) is produced in an analogous manner from o-acetylbenzoic acid and o-phenylenediamine.

Workup

  1. distillationwhile distilling off water and chlorobenzene
  2. customThe excess chlorobenzene is then removed in vacuo
  3. distillationthe residue is distilled under high vacuum
  4. customis recrystallised from a little ethyl acetate

Sources & evidence

ORD record
ord-51fd7737e6834316872403ce7d7aa0d4
Source dataset
uspto-grants-1977_11
Patent number
US04058529

Reaction notes

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