HCID 67431458, compound → HCID 58459125, compound

HRID 2036605Notes

Reaction equation

HRID 2036605 reaction equation
[CH:1]1([NH:4][C:5]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[NH2:15][C:14]1[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 67431458HCID 67431458, compound

Product 1

HCID 58459125HCID 58459125, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(cyclopropylamino)-3-nitrobenzoate (1.1 g, 4.5 mmol) in MeOH (4 mL) was added palladium 10 wt % on carbon (0.24 g, 0.23 mmol) under N2. After flushing the flask with N2 several times, the solution was stirred under a H2 balloon for 6 h. LCMS showed the reaction was complete. After filtration of the reaction mixture and rinsing with MeOH, the filtrate was collected and concentrated in vacuo. Purification of the residue by flash chromatography over silica gel column using 0-20% gradient of DCM-MeOH—NH4OH (9:1:0.05) in DCM as eluent gave methyl 3-amino-2-(cyclopropylamino)benzoate: LC-MS (ESI) m/z 207.1 [M+H]+.

Workup

  1. customAfter flushing the flask with N2 several times
  2. filtrationAfter filtration of the reaction mixture
  3. washrinsing with MeOH
  4. customthe filtrate was collected
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by flash chromatography over silica gel column

Sources & evidence

ORD record
ord-27cfdfd3609545469d2ff83e04f2d8bd
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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