HCID 690583, compound → HCID 54226184, compound

HRID 2170537Notes

Reaction equation

HRID 2170537 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([N+:15]([O-])=O)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:4].C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:15][C:13]1[CH:12]=[C:7]([CH:6]=[C:5]([C:3]([NH:2][CH3:1])=[O:4])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 2

HCID 690583HCID 690583, compound2×HCID 2723923Ammonium formate

Product 1

HCID 54226184HCID 54226184, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of methyl 3-[(methylamino)carbonyl]-5-nitrobenzoate (Intermediate 29) (1.33 g, 5.59 mmol), in ethanol (30 mL) were added ammonium formiate (3.52 g, 1 eq.) and Pd/C (catalytic quantity). The reaction was stirred at 40° C. for one night. After filtration on celite, the solvent was evaporated in vacuo. The residue was dissolved in DCM, washed with water, dried over sodium sulfate and concentrated to give the title compound as a white solid (0.56 g, 48.3%). LC/MS: m/z 209 (M+H)+, Rt: 1.50 min.

Workup

  1. filtrationAfter filtration on celite
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef6024007818421da4edb5939c74872e
Source dataset
uspto-grants-2015_06
Patent number
US09051281B2

Reaction notes

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