HCID 20202868, compound → HCID 20202886, compound

HRID 978438Notes

Reaction equation

HRID 978438 reaction equation
[N+:1]([C:4]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])([O-])=O.[H][H]>[Ni].C(O)C>[NH2:1][C:4]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 20202868HCID 20202868, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20202886HCID 20202886, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 25 parts of ethyl 2-nitro-4-(phenylmethoxy)benzoate and 160 parts of ethanol was hydrogenated at normal pressure and at room temperature with 5 parts of Raney-nickel catalyst. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95.5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was boiled in 2,2'-oxybispropane. After cooling, the product was filtered off and dried, yielding 14.5 parts (65%) of ethyl 2-amino-4-(phenylmethoxy)benzoate (4).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol (95.5 by volume) as eluent
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. temperatureAfter cooling
  8. filtrationthe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-01e3a9bee9d348f1bc5ccddce47389dd
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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