Methylhydrazine → 4-Aminooxymethyl-2-bromo-benzoic acid methyl ester

HRID 1392271Notes

Reaction equation

HRID 1392271 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([O:12][N:13]2C(=O)C3C(=CC=CC=3)C2)=O)=[CH:6][C:5]=1[Br:23].CNN>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:12][NH2:13])=[CH:6][C:5]=1[Br:23]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 691968752-Bromo-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-benzoic acid methyl ester

Product 1

HCID 691941704-Aminooxymethyl-2-bromo-benzoic acid methyl esterYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-benzoic acid methyl ester (0.40 g, 1.02 mmol) in methylene chloride (15 mL) cooled to 0° C. was added methyl hydrazine (0.087 g, 1.88 mmol). After a few minutes the ice bath was removed and the mixture was allowed to stir at room temperature for 2 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/methylene chloride (0/100 gradient to 6/94) to give 4-aminooxymethyl-2-bromo-benzoic acid methyl ester (0.25 g, 94%) as a colorless oil. 1H NMR (400 MHz, CDCl3); δ 7.79 (d, 1H), 7.66 (s, 1H), 7.32 (d, 1H), 4.67 (s, 2H), 3.92 (s, 3H).

Workup

  1. customAfter a few minutes the ice bath was removed
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-7174baf231c048b2baeb4e33e8e1e02e
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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