Water → HCID 136356821, compound

HRID 1671564Notes

Reaction equation

HRID 1671564 reaction equation
[CH:1]1([C:4]([C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH:8]=[CH:9][C:10]([NH:16][C@H:17]2[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]2)=[N:11]3)=O)[CH2:3][CH2:2]1.Cl.[NH2:27][OH:28].C(=O)([O-])[O-].[Na+].[Na+].O>C(O)C>[CH:1]1([C:4]([C:6]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:7]=2[CH:8]=[CH:9][C:10]([NH:16][C@H:17]2[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:19][CH2:18]2)=[N:11]3)=[N:27][OH:28])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 44219395HCID 44219395, compound

Product 1

HCID 136356821HCID 136356821, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of cyclopropyl-[2-((R)-indan-1-ylamino)-quinolin-5-yl]-methanone (example 30) (150 mg, 0.46 mmol), hydroxylamine hydrochloride (95 mg, 1.37 mmol) and sodium carbonate (145 mg, 1.37 mmol) in ethanol (5 ml) was heated under reflux conditions for 18 h, the reaction mixture was poured into water (5 ml) and the mixture was stirred for 2 h. The precipitate was collected by filtration and further purified by flash chromatography on silica gel (heptane/ethyl acetate) to yield the title compound as off-white solid (72 mg, 46%). M.p. 151° C.; MS: m/e=344.1 (M+H+).

Workup

  1. temperaturewas heated under reflux conditions for 18 h
  2. filtrationThe precipitate was collected by filtration
  3. customfurther purified by flash chromatography on silica gel (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-5de7b596ea4945c69a8a6fbfaa836178
Source dataset
uspto-grants-2011_08
Patent number
US07994324B2

Reaction notes

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