O-Phenylenediamine → HCID 18940605, compound

HRID 356208Notes

Reaction equation

HRID 356208 reaction equation
O=[C:2]([CH2:8][N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19])[CH2:3][C:4]([O:6]C)=O.[C:20]1([NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH2:26]>C1(C)C(C)=CC=CC=1>[C:13]1(=[O:14])[N:9]([CH2:8][C:2]2[CH2:3][C:4](=[O:6])[NH:27][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[N:26]=2)[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]12

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 2841582Methyl 3-oxo-4-phthalimidobutyrate

Product 1

HCID 18940605HCID 18940605, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of methyl 3-oxo-4-phthalimidobutyrate (15.4 g, 59 mmol), o-phenylenediamine (6.37 g, 59 mmol) and xylene (150 mL) was refluxed for 20 minutes using Dean-Stark apparatus. The reaction mixture was cooled, and resulting crystals were collected by filtration and washed with toluene to give the object compound (15.36 g, 81%), m.p.244°-246° C.

Workup

  1. temperaturewas refluxed for 20 minutes
  2. temperatureThe reaction mixture was cooled
  3. customresulting crystals
  4. filtrationwere collected by filtration
  5. washwashed with toluene

Sources & evidence

ORD record
ord-cc59e5df25e04b23983c00e6c5e1cae6
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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