Toluene → HCID 19862798, compound

HRID 1165262Notes

Reaction equation

HRID 1165262 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[N+:16]([O-])=O.C1(C)C=CC=CC=1.[H][H]>[Pd].O1CCCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6](=[O:19])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[NH2:16]

Participants

6

Reactant 3

HCID 1140TolueneHCID 19862794HCID 19862794, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19862798HCID 19862798, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A two liter autoclave was charged with 142 g of (3-chloropropyl)-2,4-dinitrobenzoate, 1275 ml of toluene and 4.5 g of a 5% palladium on carbon/50% water catalyst. The mixture was hydrogenated at 800 psi hydrogen pressure while maintaining the temperature below 100° C. with cooling. The mixture was cooled and 350 ml of tetrahydrofuran was added to dissolve the solid that had precipitated from the toluene. The resulting solution was filtered to remove the catalyst and the solvents removed at reduced pressure to give 113 g of (3-chloropropyl)-2,4-diaminobenzoate, a white solid, mp 97° C.

Workup

  1. temperaturewhile maintaining the temperature below 100° C.
  2. temperaturewith cooling
  3. temperatureThe mixture was cooled
  4. dissolutionto dissolve the solid
  5. customthat had precipitated from the toluene
  6. filtrationThe resulting solution was filtered
  7. customto remove the catalyst
  8. customthe solvents removed at reduced pressure

Sources & evidence

ORD record
ord-df1d3e4b78b2434f92c165ee2f937e84
Source dataset
uspto-grants-1990_03
Patent number
US04908394

Reaction notes

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