Glyoxylic Acid → O-2-[Z-5-fluoro-2-methyl-1-(4-pyridyl)methylene-1H-inden-3-yl]ethyl hydroxylamine

HRID 1292277Notes

Reaction equation

HRID 1292277 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=O)[CH:6]([CH3:12])[CH2:5]2.[N:13]1[CH:18]=[CH:17][C:16]([CH2:19][Mg]Cl)=[CH:15][CH:14]=1.[C:22]([OH:26])(=O)[CH:23]=O.[NH2:27]O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:19]\[C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1)/[C:6]([CH3:12])=[C:5]2[CH2:23][CH2:22][O:26][NH2:27]

Participants

6

Reactant 4

HCID 760Glyoxylic AcidHCID 787HydroxylamineHCID 30162575-Fluoro-2-methylindan-1-oneHCID 178479002HCID 178479002, compound

Product 1

HCID 86752651O-2-[Z-5-fluoro-2-methyl-1-(4-pyridyl)methylene-1H-inden-3-yl]ethyl hydroxylamine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound is prepared by Grignard reaction of 5-fluoro-2-methylindanone with 4-pyridylmethylmagnesium chloride to provide the intermediate adduct which is treated with glyoxalic acid under dehydrating aldol conditions to provide Z-5-fluoro-2-methyl-1-(4-pyridyl)methylene-1H-inden-3-yl!acetic acid which is converted to the hydroxylamine by the procedures described in Example 1.

Workup

  1. customto provide the intermediate adduct which
  2. customto provide Z-5-fluoro-2-methyl-1-(4-pyridyl)methylene-1H-inden-3-yl

Sources & evidence

ORD record
ord-8305cd1fa12b4cd891197daf8e51a66a
Source dataset
uspto-grants-1998_05
Patent number
US05756531

Reaction notes

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