Potassium Hydroxide → HCID 66803944, compound

HRID 1843914Notes

Reaction equation

HRID 1843914 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1.[OH:32][C:33]1[CH:42]=[C:41]2[C:36]([CH2:37][CH2:38][N:39]([C:44]3[CH:45]=[N:46][CH:47]=[CH:48][C:49]=3[CH3:50])[C:40]2=[O:43])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1.CCCCCC.C(OC(=O)C)C>[CH3:50][C:49]1[CH:48]=[CH:47][N:46]=[CH:45][C:44]=1[N:39]1[CH2:38][CH2:37][C:36]2[C:41](=[CH:42][C:33]([O:32][C:2]3[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=3)=[CH:34][CH:35]=2)[C:40]1=[O:43]

Participants

8

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 1449582-Chloro-4-(trifluoromethyl)pyridineHCID 56942892HCID 56942892, compound

Product 1

HCID 66803944HCID 66803944, compoundYield 12.8%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

2-Chloro-4-trifluoromethyl-pyridine (97 mg, 0.59 mmol), KOH (26.4 mg, 0.471 mmol) and 18-crown-6-ether (156 mg, 0.59 mmol) were added to a solution of 7-hydroxy-2-(4-methyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (35B: 100 mg, 0.393 mmol) in toluene (3 mL). The resulting mixture was heated to 110° C. for 3 hours. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was filtered and the filtrate was concentrated to afford the crude product. Purification by column chromatography on silica gel (30% ethylacetate in hexane) afforded 20 mg of the product (12.8% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto afford the crude product
  4. customPurification by column chromatography on silica gel (30% ethylacetate in hexane)

Sources & evidence

ORD record
ord-d4918910897c40a085a2fe0c7144bff8
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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