Chloromethyl Methyl Ether → HCID 23300505, compound
Reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:20]=[C:19]2C([C:15](O)=[C:16]([O:23]C(=O)C)[C:17](=O)[N:18]2C)=[CH:13][CH:12]=1)([O-:10])=[O:9].C[O:29]CCl.[CH2:32]1[CH2:36][O:35][CH2:34][CH2:33]1>>[C:16]([CH2:17][NH:18][C:19]1[CH:20]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=[CH:13][C:33]=1[C:34]([O:35][CH2:36][CH3:32])=[O:29])(=[O:23])[CH3:15]Participants
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 (yield=54%) residue was crystallized from THF and hexane to yield 1.45 g of the title compound (18). (yield=54%)
Workup
- additionwas dropped to the mixture
- filtrationFiltration of the reaction mixture
- concentrationthe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-307d3f6511d74f76966c88ce8332c571
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05942521
Reaction notes
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