Chloromethyl Methyl Ether → HCID 23300344, compound

HRID 1952824Notes

Reaction equation

HRID 1952824 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([OH:27])=[C:16]([O:23][C:24](=[O:26])[CH3:25])[C:17](=[O:22])[N:18]2[CH3:21])=[CH:13][CH:12]=1)([O-:10])=[O:9].[CH3:28][O:29][CH2:30]Cl>C1COCC1>[N+:8]([C:11]1[CH:20]=[C:19]2[C:14]([C:15]([O:27][CH2:28][O:29][CH3:30])=[C:16]([O:23][C:24](=[O:26])[CH3:25])[C:17](=[O:22])[N:18]2[CH3:21])=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 8471TriethylamineHCID 54713869HCID 54713869, compound

Product 1

HCID 23300344HCID 23300344, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After addition of 1.87 g of triethylamine (18.5 mmol) to a mixture of 3.2 g of 7-nitro-3-acetoxy-4-hydroxy-1-methyl-2(1H)-quinolinone (11.5 mmol) in 64 ml of THF, 1.89 g of chloromethyl methyl ether (23.0 mmol) was dropped to the mixture, and stirred at room temperature for 1 hour. Filtration of the reaction mixture, the filtrate was concentrated under reduced pressure to give 3.6 g of 7-nitro-3-acetoxy-4-methoxymethoxy-1-methyl-2(1H)-quinolinone. In accordance with EXAMPLE 4, the obtained 7-nitro-3-acetoxy-4-methoxymethoxy-1-methyl-2(1H)-quinolinone was used instead of 7-nitro-3-acetoxy-4-hydroxy-1-methyl-2(1H)-quinolinone, 7-nitro-3-hydroxy-4-methoxymethoxy-1-methyl-2(1H)-quinolinone was provided. Then in accordance with EXAMPLE 2, 7-nitro-3-methoxy-4-methoxymethoxy-1-methyl-2(1H)-quinolinone was given by methylation reaction. Finally, to a mixture of the obtained 7-nitro-3-methoxy-4-methoxymethoxy-1-methyl-2(1H)-quinolinone in 40 ml of methanol was added 0.22 g of p-toluenesulfonic acid monohydrate and stirred at room temperature for 1 hour. To the reaction mixture was added water, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was crystallized from THF and hexane to yield 1.45 g of the title compound (18). (yield=54%)

Workup

  1. additionwas dropped to the mixture
  2. filtrationFiltration of the reaction mixture
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-529ab354160c4914a82c678e1b8a8f2b
Source dataset
uspto-grants-2000_09
Patent number
US06114352

Reaction notes

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