Methyl 3-(benzyloxy)-4-nitrobenzoate → Methyl 4-amino-3-(benzyloxy)benzenecarboxylate

HRID 1814355Notes

Reaction equation

HRID 1814355 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[C:6]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:5]=1>[Ni].O1CCCC1>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=1

Participants

4

Reactant 1

HCID 15054012Methyl 3-(benzyloxy)-4-nitrobenzoate

Product 1

HCID 25052945Methyl 4-amino-3-(benzyloxy)benzenecarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (100 mL) of 3-benzyloxy-4-nitro-benzoic acid methyl ester(10.0 g, 34.9 mmol) was added Raney Nickel (wet) (2.0 g). The reaction was pressured to approximately 50 psi at left to shake at room temperature for 5.5 h. An aliquot was removed and TLC deemed the reaction complete. The reaction was filtered through celite and then concentrated under reduced pressure to yield 4-amino-3-benzyloxy-benzoic acid methyl ester as a solid (8.7 g, 97%). 1H NMR (CDCl3) 7.58(m,2H), 7.50-7.30(m,5H), 6.70(d,1H), 5.14(s,2H), 4.84(s,3H).

Workup

  1. waitat left
  2. customAn aliquot was removed
  3. filtrationThe reaction was filtered through celite
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ec255ef11a84ce8afe24c1252a1630f
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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