Water → HCID 66668516, compound

HRID 924648Notes

Reaction equation

HRID 924648 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:17][C:16](=[O:32])[CH2:15]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[OH:10])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:40][O:41][CH3:42].O>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:14]2[C:19]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:18]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[NH:17][C:16](=[O:32])[CH2:15]2)[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[O:10][CH2:40][O:41][CH3:42])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 56644284HCID 56644284, compound2×

Product 1

HCID 66668516HCID 66668516, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-(3-ethoxy-4-hydroxy-5-nitrophenyl)-5,6-diphenyl-3,4-dihydropyridin-2(1H)-one (Compound 1, see Example 1) (200 mg, 0.47 mmol) and potassium carbonate (130 mg, 0.93 mmol) in DMF (5 mL) was added chloro(methoxy)methane (75 mg, 0.93 mmol) at 25° C. and then the mixture was stirred at the same temperature for 2 hours. The mixture was poured into water and a standard aqueous/EtOAc workup was followed to give product (200 mg, 98%).

Sources & evidence

ORD record
ord-4c11849f80764a17af6e54bfe71ae0b2
Source dataset
uspto-grants-2016_03
Patent number
US09283213B2

Reaction notes

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