Water → HCID 86682979, compound

HRID 1497138Notes

Reaction equation

HRID 1497138 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][C:9]=2[CH3:22])=[O:4].[Cu][C:25]#[N:26].O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:23])[NH:7][C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:25]#[N:26])=[CH:10][C:9]=2[CH3:22])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 86682977HCID 86682977, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 86682979HCID 86682979, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A suspension of 6-bromo-8-methyl-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid methyl ester (prepared as described in example 54 step C) (140 mg, 376 μmol, Eq: 1.00) and copper(I) cyanide (121 mg, 41.5 μl, 1.35 mmol, Eq: 3.6) in DMF (2.8 ml) was heated to 130° C. for 2 d. Then water was added and the mixture was extracted with DCM (3×). The combined extracts were washed with water and brine, dried with Na2SO4 and evaporated to give the title compound as off-white solid (120 mg). MS (ESI): 317.2 (M−H)−

Workup

  1. extractionthe mixture was extracted with DCM (3×)
  2. washThe combined extracts were washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-9f511029469049c788b3e5b18e512344
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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