HCID 21328271, compound → HCID 21328272, compound

HRID 614633Notes

Reaction equation

HRID 614633 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:7](=[CH:12][C:13]=1[C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]([O:10][CH3:11])=[O:9])([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([C:18]([O:20][CH3:21])=[O:19])[C:7](=[CH:12][C:13]=1[C:14]([CH3:17])([CH3:15])[CH3:16])[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 21328271HCID 21328271, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21328272HCID 21328272, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl 4-nitro-5-t-butylphthalate (42 g.) was mixed with 0.2 g. of 5% Pd/C and, while kept under argon, 200 ml. of methanol was added. Rapid stirring under 30 psi of hydrogen gave complete reduction after 20 hours at 35° C. The mixture was filtered through Celite, and the methanol removed under reduced pressure. The residue was dissolved in 250 ml. of hot benzene, filtered, and mixed with 500 ml. of hexane. After standing 3 hours at room temperature and 16 hours at -10° C., the crystalline product was filtered off. After drying, 35.8 g. (95%) of solid dimethyl 4-amino-5-t-butylphthalate remained, m.p. 120°-122° C.

Workup

  1. customgave complete reduction after 20 hours at 35° C
  2. filtrationThe mixture was filtered through Celite
  3. customthe methanol removed under reduced pressure
  4. dissolutionThe residue was dissolved in 250 ml
  5. filtrationof hot benzene, filtered
  6. additionmixed with 500 ml
  7. filtrationthe crystalline product was filtered off
  8. customAfter drying

Sources & evidence

ORD record
ord-c1774333860c434e93222b797de2d43b
Source dataset
uspto-grants-1979_03
Patent number
US04145522

Reaction notes

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