HCID 14574473, compound → HCID 178497326, compound

HRID 259705Notes

Reaction equation

HRID 259705 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:19]([O-])=O)=[C:7]([C:15]([O:17][CH3:18])=[O:16])[C:8](=[CH:13][CH:14]=1)[C:9]([O:11][CH3:12])=[O:10])(=O)[CH3:2]>CO.[Pt].C(O)(=O)C.C1(C)C=CC=CC=1>[CH3:2][C:1]1[NH:19][C:6]2[C:5](=[CH:14][CH:13]=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:7]=2[C:15]([O:17][CH3:18])=[O:16])[N:4]=1

Participants

6

Reactant 1

HCID 14574473HCID 14574473, compound

Product 1

HCID 178497326HCID 178497326, compoundYield 60.1%

Reagents, catalysts & solvents 4

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of dimethyl 4-acetamido-3-nitrophthalate (142.1 g, 0.480 mol) in methanol with 5% platinum on carbon catalyst is hydrogenated on a Parr hydrogenator at room temperature. The reaction mixtures is filtered through diatomaceous earth and concentrated in vacuo to afford a solid residue. This solid is dispersed in glacial acetic acid and toluene, and heated with stirring at reflux temperatures for 4 hours with azeotropic removal of water. The resultant hot reaction mixture is slowly added to a saturated sodium bicarbonate solution with vigorous stirring, filtered and the filter cake dried to give the title product as a white solid (71.6 g, 60.1%), mp 97°-103° C.

Workup

  1. customis hydrogenated on a Parr hydrogenator at room temperature
  2. customThe reaction mixtures
  3. filtrationis filtered through diatomaceous earth
  4. concentrationconcentrated in vacuo
  5. customto afford a solid residue
  6. temperatureat reflux temperatures for 4 hours
  7. customwith azeotropic removal of water
  8. additionThe resultant hot reaction mixture is slowly added to a saturated sodium bicarbonate solution with vigorous stirring
  9. filtrationfiltered
  10. customthe filter cake dried

Sources & evidence

ORD record
ord-ad91672629d34457b9f18f3982367648
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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