Water → Methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoate

HRID 732187Notes

Reaction equation

HRID 732187 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Br)([O-])=O.O>CN(C)C=O.[Pt](=O)=O.C(O)C.O1CCCC1>[NH2:16][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

Product 1

HCID 23143302Methyl 3-{4-[(3-aminobenzyl)oxy]phenyl}-propanoateYield 96%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (5.10 g, 28.3 mmol) in N,N-dimethylformamide (40 mL) was added sodium hydride (in oil, 1.20 g, 30 mmol) at 0° C. and the mixture was stirred at the same temperature for 1 hr. 3-Nitrobenzylbromide (6.72 g, 31.1 mmol) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a yellow oil. To a mixture of the obtained oil, tetrahydrofuran (50 mL) and ethanol (50 mL) was added platinum dioxide (350 mg) and the mixture was stirred under a hydrogen atmosphere for 16 hr. Insoluble materials were filtered off, and the filtrate was concentrated to give the title compound (7.73 g, yield 96%, 2 steps) as pale-yellow crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. stirringthe mixture was stirred under a hydrogen atmosphere for 16 hr
  8. filtrationInsoluble materials were filtered off
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7e6a04f450a14aeda5744ec4e4a652d5
Source dataset
uspto-grants-2009_09
Patent number
US07585880B2

Reaction notes

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