Methyl 3-(N'-hydroxycarbamimidoyl)-4-methylbenzoate → Methyl 3-carbamimidoyl-4-methylbenzoate

HRID 541185Notes

Reaction equation

HRID 541185 reaction equation
O[N:2]=[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])[NH2:4]>CO>[C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])(=[NH:2])[NH2:4]

Participants

3

Reactant 1

HCID 86672520Methyl 3-(N'-hydroxycarbamimidoyl)-4-methylbenzoate2×

Product 1

HCID 68288326Methyl 3-carbamimidoyl-4-methylbenzoateYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A round-bottom flask, containing a solution of methyl 3-(N′-hydroxycarbamimidoyl)-4-methylbenzoate (compound 1.8, 8 g, 36.50 mmol, 1.00 equiv, 95%) in methanol (150 mL) was purged with nitrogen gas. To the solution was added palladium on carbon (9 g, 10%, 60% water) and the flask was then further purged with nitrogen gas. The atmosphere was then changed to hydrogen and the mixture was stirred overnight at 25° C. under a balloon. After purging the system with nitrogen, the solids were removed by filtration and the filtrate was concentrated under reduced pressure to yield 4 g (54%) of the title compound as a brown solid.

Workup

  1. customwas purged with nitrogen gas
  2. additionTo the solution was added palladium on carbon (9 g, 10%, 60% water)
  3. customthe flask was then further purged with nitrogen gas
  4. customAfter purging the system with nitrogen
  5. customthe solids were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ce747048371c4dd2a007705e0ff13e67
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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