HCID 10160091, compound → HCID 87858589, compound

HRID 1594498Notes

Reaction equation

HRID 1594498 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([CH:11]([O:20]C(=O)C(Cl)(Cl)Cl)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:5]([N+:27]([O-])=[O:28])[CH:4]=1.[CH3:30][O:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([CH:40]([O:47]C(=O)C(Cl)(Cl)Cl)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:34]([N+:54]([O-])=[O:55])[CH:33]=1>C(#N)C>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[O:20])=[C:5]([N:27]=[O:28])[CH:4]=1.[CH3:30][O:31][C:32]1[C:37]([O:38][CH3:39])=[CH:36][C:35]([C:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:47])=[C:34]([N:54]=[O:55])[CH:33]=1

Participants

5

Reactant 2

HCID 10160091HCID 10160091, compoundHCID 69497536HCID 69497536, compound

Product 2

HCID 87858589HCID 87858589, compoundHCID 87858622HCID 87858622, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Irradiation of 0.2% solutions of α-(3-methoxyphenyl)-4,5-dimethoxy-2-nitrobenzyltrichloroacetate (38) and α-phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate (39) in acetonitrile resulted in nearly quantitative conversions into the expected photoproducts, 4,5-dimethoxy-3′-methoxy-2-nitrosobenzophenone (50) and 4,5-dimethoxy-2-nitrosobenzophenone (51), respectively, after less than 4 minutes. Irradiations at lower concentrations, monitored by UV, resulted in even faster photoreactions. When a 0.004% solution of α-phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate (39) was irradiated, there was a quantitative conversion into the photoproduct after 30 seconds. The two esters appeared to have a similar rate of photoconversion but the photolysis of α-phenyl-4,5-dimethoxy-2-nitrobenzyltrichloroacetate (39), quantum yield φ˜0.14, was cleaner with less amount of polar secondary photoproducts. These properties, coupled with the reduced inner filter effect and absorption maximum at 345 nm, make compound 39 a prime candidate for use in the microarray format.

Sources & evidence

ORD record
ord-e10d965524824ccfa91492aa66c8a8bc
Source dataset
uspto-grants-2007_11
Patent number
US07301049B2

Reaction notes

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