HCID 15225858, compound → HCID 15208142, compound

HRID 1459899Notes

Reaction equation

HRID 1459899 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][N:16]=[N+]=[N-])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][NH2:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 15225858HCID 15225858, compound

Product 1

HCID 15208142HCID 15208142, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred suspension of crude 10 (0.77 g) and 10% Pd on carbon (0.07 g) in methanol (5 mL) was degassed at room temperature and then subjected to 1 atm of hydrogen gas via inflated balloon for 12 h. Excess hydrogen was removed under vacuum and the reaction vessel was purged with argon. The reaction mixture was filtered through filter agent Celatom FW-14 with methanol washings to remove catalyst. The filtrate was concentrated under reduced pressure to provide 0.60 g of methyl 3,5-bis(aminomethyl)benzoate (11) as a pale yellow oil. The crude product was used without further purification; IR(thin film): 3357, 3296, 2951, 1721, 1651, 1602, 1544, 1435, 1307, 1224 cm-1 ; PMR (DMSO-d6) δ7.76 (s, 2 H), 7.56 (s, 1 H), 3.85 (s, 4 H), 3.79 (s, 3 H).

Workup

  1. customwas degassed at room temperature
  2. customExcess hydrogen was removed under vacuum
  3. customthe reaction vessel was purged with argon
  4. filtrationThe reaction mixture was filtered
  5. filtrationthrough filter agent Celatom FW-14 with methanol washings
  6. customto remove catalyst
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63ddb6e3b06a4b6d978c7bd6289a1a32
Source dataset
uspto-grants-1998_12
Patent number
US05854410

Reaction notes

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