HCID 19068877, compound → HCID 19068901, compound

HRID 1957127Notes

Reaction equation

HRID 1957127 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([CH3:15])=[C:8]([CH3:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]>ClCCl.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([CH3:15])=[C:8]([CH3:16])[C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 19068877HCID 19068877, compound

Product 1

HCID 19068901HCID 19068901, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2-amino-5,6-dimethyl-3-nitrobenzoate (11.78 g, 52.5 mmol) in dichloromethane (525 mL) was hydrogenated over 10% palladium on charcoal (1.2 g) at 50 psi (3.3 atm) and 50° C. for 16 hours. Another portion of catalyst (1.2 g) was added, and hydrogenation was allowed to proceed for a further 16 hours. The mixture was filtered through Arbocel filter aid, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with dichloromethane/methanol) to give methyl 2,3-diamino-5,6-dimethylbenzoate (8.36 g, 82%) as an orange oil.

Workup

  1. filtrationThe mixture was filtered through Arbocel
  2. filtrationfilter aid
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (gradient elution with dichloromethane/methanol)

Sources & evidence

ORD record
ord-cb837a294ce1424f91ade9fec9e4b7ef
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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