HCID 67281915, compound → HCID 67283096, compound

HRID 1616149Notes

Reaction equation

HRID 1616149 reaction equation
[CH:1]([NH:4][C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][C:8]=1[N+:17]([O-])=O)=[O:6])([CH3:3])[CH3:2]>CO.O1CCCC1.[Pd]>[NH2:17][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:7]=1[C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 1

HCID 67281915HCID 67281915, compound

Product 1

HCID 67283096HCID 67283096, compoundYield 99.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(isopropylamino)carbonyl]-3-nitrobenzoate (0.48 g, 1.78 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL) was added 10% palladium on carbon (0.19 g, 0.18 mmol). The mixture was purged with H2 gas (3×) and stirred under an atmosphere of H2 for 1 d. The reaction mixture was then filtered through Celite, washed with MeOH and concentrated to afford methyl 3-amino-4-[(isopropylamino)carbonyl]benzoate (0.42 g, quant.). LC-MS: (FA) ES+ 237.

Workup

  1. customThe mixture was purged with H2 gas (3×)
  2. filtrationThe reaction mixture was then filtered through Celite
  3. washwashed with MeOH
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f57e3ee0f0de4820b08f732ec4c774c1
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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