Methylhydrazine → 6-(3-Aminooxy-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

HRID 1392287Notes

Reaction equation

HRID 1392287 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)[C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][N:16]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:9][CH:10]=1)=[O:4].CNN>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:27]2[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:36])[F:35])=[CH:31][CH:32]=2)[C:8]([O:11][CH2:12][CH2:13][CH2:14][O:15][NH2:16])=[CH:9][CH:10]=1)=[O:4]

Participants

3

Reactant 2

HCID 6061MethylhydrazineHCID 691957396-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 691944346-(3-Aminooxy-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl esterYield 92.1%

Procedure

This compound was produced using similar methods as those used in Step 2, example 4, starting with 6-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.50 g, 1.00 mmol) and methyl hydrazine (0.087 g, 1.88 mmol). The crude material was purified by flash chromatography through silica gel using ethyl acetate/methylene chloride (2/98 gradient to 8/92) to give 6-(3-aminooxy-propoxy)-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.34 g, 92%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-6216646b087b49cd860d7ecf09e6de47
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

Loading…