Water → HCID 136348771, compound

HRID 1170215Notes

Reaction equation

HRID 1170215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][C:14]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])=[N:15]3)=O)=[CH:4][CH:3]=1.Cl.[NH2:31][OH:32].C(=O)([O-])[O-].[Na+].[Na+].O>CCO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][C:14]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])=[N:15]3)=[N:31][OH:32])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 24991561HCID 24991561, compound

Product 1

HCID 136348771HCID 136348771, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of (4-fluoro-phenyl)-[2-(2-methoxy-benzylamino)-quinolin-5-yl]-methanone (example 137) (60 mg, 0.155 mmol), hydroxylamine hydrochloride (32 mg, 0.46 mmol) and sodium carbonate (49 mg, 0.46 mmol) in EtOH (2 ml) was heated under reflux conditions for 28 h, the reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate) to yield the title compound as white foam (40 mg, 64%).

Workup

  1. temperaturewas heated under reflux conditions for 28 h
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layers were washed with brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a92d22082bae459488b7bc31ac27afe6
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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