Potassium Hydroxide → HCID 86683006, compound

HRID 1497172Notes

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]([CH:17]([CH3:19])[CH3:18])[CH:12]=1)=O.[C:20]([O:24][C:25](=[O:34])[CH2:26][C:27](OC(C)(C)C)=[O:28])([CH3:23])([CH3:22])[CH3:21].[OH-].[K+]>>[C:20]([O:24][C:25]([C:26]1[C:27](=[O:28])[NH:1][C:2]2[C:3]([C:9]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([CH3:19])[CH3:18])[CH:12]=1)=[CH:4][C:5]([Cl:8])=[CH:6][CH:7]=2)=[O:34])([CH3:23])([CH3:22])[CH3:21]

Participants

Reactant 3

HCID 14797Potassium Hydroxide

HCID 68324Di-tert-butyl malonate

HCID 86683005HCID 86683005, compound

Product 1

HCID 86683006HCID 86683006, compoundYield 44%

Conditions

Temperature: 110 °C

Procedure

To a mixture of (2-amino-5-chloro-phenyl)-(3-isopropyl-phenyl)-methanone (1.1 g, 4.02 mmol), and malonic acid di-tert-butyl ester (1.344 ml, 6.03 mmol) was added potassium hydroxide (113 mg, 2.01 mmol) at 25° C., and the resulting reaction mixture was stirred at 110° C. for 16 h. It was cooled to 0° C., and directly purified by column chromatography over silica gel (20-30% EtOAc/hexane) to afford 6-chloro-4-(3-isopropyl-phenyl)-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid tert-butyl ester (700 mg, 44%) as pale yellow solid. LC-MS (ESI): 398 (M+H)+.

Workup

customthe resulting reaction mixture
temperatureIt was cooled to 0° C.
customdirectly purified by column chromatography over silica gel (20-30% EtOAc/hexane)

Sources & evidence

ORD record: ord-bad481c8dac84c50b978876c39e5b737
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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