Hydroxyamine hydrochloride → HCID 136167019, compound

HRID 1617623Notes

Reaction equation

HRID 1617623 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](I)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.C([Li])CCC.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:26][C:27]([N:29]([O:31]C)C)=O)=[CH:21][CH:20]=1.Cl.NO.C([O-])(O)=O.[Na+]>>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[CH3:39])[CH2:26]/[C:27](/[C:6]2[C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[N:29]\[OH:31])=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 111853697-Chloro-4-iodoquinolineHCID 866609493-(4-Bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamideHCID 178418339Butyllithium

Product 1

HCID 136167019HCID 136167019, compound

Procedure

In analogy to example 151, step 1, 7-chloro-4-iodoquinoline was reacted first with n-butyllithium and later with 3-(4-bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide (example 74, step 4). The product of this reaction could not be obtained pure and was reacted in analogy to example 151, step 3, with hydroxylamine hydrochloride in the presence of NaHCO3 to give the title compound containing less than 10% of the corresponding Z isomer as a colorless solid, MS (ESI−): m/z=478.9 [M−H]−.

Workup

  1. customThe product of this reaction could not
  2. custombe obtained pure

Sources & evidence

ORD record
ord-4a581367c8d6448594dc1c60d35b9e31
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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