Methylhydrazine → 4-(3-Aminooxy-propoxy)-2-hydroxy-benzoic acid methyl ester

HRID 1392277Notes

Reaction equation

HRID 1392277 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][N:15]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][C:5]=1[OH:26].CNN>>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][O:14][NH2:15])=[CH:6][C:5]=1[OH:26]

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 691957184-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-2-hydroxy-benzoic acid methyl ester

Product 1

HCID 691961504-(3-Aminooxy-propoxy)-2-hydroxy-benzoic acid methyl esterYield 96.2%

Procedure

This compound was produced using similar methods as those used in Step 2, example 4, starting with 4-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-2-hydroxy-benzoic acid methyl ester (0.42 g, 1.12 mmol) and methyl hydrazine (0.087 g, 1.88 mmol). The crude material was purified by flash chromatography through silica gel using ethyl acetate/chloroform (10/90) to give 4-(3-aminooxy-propoxy)-2-hydroxy-benzoic acid methyl ester (0.26 g, 96%) as a white solid. 1H NMR (400 MHz, CDCl3); δ 7.51 (d, 1H), 6.23 (s, 1H), 6.21 (d, 1H), 3.85 (t, 2H), 3.69 (s, 3H), 3.62 (t, 2H), 1.86 (m, 2H).

Workup

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-0be70e24f5734b24a106aea0af7ef806
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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