Hydroxyamine hydrochloride → HCID 59846159, compound

HRID 1697109Notes

Reaction equation

HRID 1697109 reaction equation
[CH2:1]([C:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3C(C)=CC=C3C)[N:21]=2)[C:9]=1[C:33]1[O:34][CH:35]=[CH:36][N:37]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO>CCO.O>[NH2:26][C:22]1[N:21]=[C:20]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([Cl:19])[CH:12]=3)[C:17](=[O:18])[C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:33]2[O:34][CH:35]=[CH:36][N:37]=2)[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 66816934HCID 66816934, compound

Product 1

HCID 59846159HCID 59846159, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-benzyl-7-chloro-1-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-yl]-2-oxazol-2-yl-1H-quinolin-4-one (640 mg) in EtOH (3.5 mL) and water (1.3 mL) and hydroxylamine hydrochloride (450 mg) was stirred for 48 h at 60° C. After evaporation of volatiles, the dark brown residue was partitioned into EtOAc and H2O, and the organic phase adsorbed on silica to provide 1-(6-amino-pyridin-2-yl)-3-benzyl-7-chloro-2-oxazol-2-yl-1H-quinolin-4-one (Compound 141). M+H=428; mp=279.3-282.8° C.

Workup

  1. customAfter evaporation of volatiles
  2. customthe dark brown residue was partitioned into EtOAc and H2O

Sources & evidence

ORD record
ord-f87d6ac64829472bba62e3e504d8b8e2
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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