Ethanol → 4,5-Diamino-2-methyl-benzoic acid methyl ester

HRID 1396655Notes

Reaction equation

HRID 1396655 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N+:12]([O-])=O)[C:9]([N+:15]([O-])=O)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(O)C>[Pd].O1CCOCC1>[CH3:1][C:2]1[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][C:9]([NH2:15])=[C:10]([NH2:12])[CH:11]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 58111280HCID 58111280, compound

Product 1

HCID 585752204,5-Diamino-2-methyl-benzoic acid methyl esterYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 5.3 g of methyl 2-methyl-4,5-dinitrobenzoate, 1.06 g of 10% palladium on carbon (50% water wet), 53 mL of ethanol, and 53 mL of 1,4-dioxane was vigorously stirred at room temperature overnight under a hydrogen atmosphere. The insoluble material was filtered and washed with methanol. The filtrate was concentrated, and then dried under reduced pressure to obtain 3.98 g of methyl 4,5-diamino-2-methyl benzoate.

Workup

  1. filtrationThe insoluble material was filtered
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3e605ae740d544ae92465aec80589855
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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