Potassium Hydroxide → HCID 178450776, compound

HRID 1497208Notes

Reaction equation

HRID 1497208 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=O.[OH-].[K+].[C:20]([O:24][C:25](=[O:34])[CH2:26][C:27](OC(C)(C)C)=[O:28])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25]([C:26]1[C:27]([OH:28])=[N:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:34])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 14797Potassium HydroxideHCID 68324Di-tert-butyl malonateHCID 5231029(2-Amino-5-chlorophenyl)(3-chlorophenyl)methanone

Product 1

HCID 178450776HCID 178450776, compoundYield 51%

Conditions

Temperature
110 °C

Procedure

A mixture of (2-amino-5-chloro-phenyl)-(3-chloro-phenyl)-methanone (550 mg, 2.07 mmol), KOH (58 mg, 1.03 mmol) and malonic acid di-tert-butyl ester (0.7 ml, 3.1 mmol) was placed in a sealed tube, and the resulting reaction mixture was stirred at 110° C. for 16 h. After cooling, the reaction mixture was purified by flash column chromatography (20-30% ethyl acetate in hexane) to give 6-chloro-4-(3-chloro-phenyl)-2-hydroxy-quinoline-3-carboxylic acid tert-butyl ester (410 mg, 51%) as an off white solid. LC-MS (ESI): 390 (M+H)+.

Workup

  1. customwas placed in a sealed tube
  2. customthe resulting reaction mixture
  3. temperatureAfter cooling
  4. customthe reaction mixture was purified by flash column chromatography (20-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5675185a3dc94cc297f34b19e9b79c5f
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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