Methyl 2-[(4-nitronaphthalen-1-yl)oxy]acetate → Methyl 2-((4-aminonaphthalen-1-yl)oxy)acetate

HRID 1171402Notes

Reaction equation

HRID 1171402 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([N+:16]([O-])=O)=[CH:8][CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:19])[CH2:4][O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([NH2:16])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 59553182Methyl 2-[(4-nitronaphthalen-1-yl)oxy]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 59553142Methyl 2-((4-aminonaphthalen-1-yl)oxy)acetateYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(4-Nitro-naphthalen-1-yloxy)-acetic acid methyl ester (0.90 g) and 10% Pd/C (90 mg) in MeOH (150 ml) is stirred at room temperature under 1 atmosphere of hydrogen for 4 h. The mixture is then filtered through Celite® and evaporated to dryness to provide (4-amino-naphthalen-1-yloxy)-acetic acid methyl ester (0.72 g). MS 232 (M+1).

Workup

  1. filtrationThe mixture is then filtered through Celite®
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-83aea31b3e8147c49dbede96beb4da31
Source dataset
uspto-grants-2010_11
Patent number
US07829560B2

Reaction notes

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