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

HRID 1189449Notes

Reaction equation

HRID 1189449 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>[NH2:12][C:10]1[C:9]([NH2:15])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([CH3:1])[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% wet), 53 mL of ethanol, and 53 mL of dioxane was thoroughly stirred at room temperature under a hydrogen atmosphere. The insoluble materials were filtered and washed sufficiently with methanol. The filtrate and the washing liquid were concentrated together, and then dried under reduced pressure to obtain 3.98 g of methyl 4,5-diamino-2-methylbenzoate.

Workup

  1. filtrationThe insoluble materials were filtered
  2. washwashed sufficiently with methanol
  3. concentrationThe filtrate and the washing liquid were concentrated together
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-7b067eedd45c4cfd87a2f8c3a0b07987
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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