Dichloromethane → Methyl 3-methoxyiminomethyl-4-nitrobenzoate

HRID 363491ノート

反応式

HRID 363491 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7])=O.C(Cl)Cl.Cl.[O:20]([NH2:22])[CH3:21].C([O-])(=O)C.[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C.O>[CH3:21][O:20][N:22]=[CH:1][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7]

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 10867527Methyl 3-formyl-4-nitrobenzoate

生成物 1

HCID 53889174Methyl 3-methoxyiminomethyl-4-nitrobenzoate収率 98.8%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

To a well stirred mixture of 195 g of methyl 3-formyl-4-nitrobenzoate, 1 l methylene chloride and 370 mL of water was added sequentially 77.6 g of methoxylamine hydrochloride, 76.2 g of sodium acetate and 6.8 g of tetra-n-butylammonium hydrogen sulfate. The resulting mixture was stirred overnight at room temperature, then diluted with 2 l of ethyl ether. The organic phase was separated and washed sequentially with water (1×500 mL), 2% aqueous hydrochloric acid (2×500 mL), water (2×250 mL), and brine (1×250 mL); then dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator yielding 218.6 g of the expected methyl 3-methoxyiminomethyl-4-nitrobenzoate as a reddish oil that solidified upon standing, and which was used as such in the next step.

後処理

  1. stirringThe resulting mixture was stirred overnight at room temperature
  2. customThe organic phase was separated
  3. washwashed sequentially with water (1×500 mL), 2% aqueous hydrochloric acid (2×500 mL), water (2×250 mL), and brine (1×250 mL)
  4. dry with materialthen dried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. customa rotary evaporator

出典と根拠

ORDレコード
ord-262721da2fde40a0b7676296280e478a
出典データセット
uspto-grants-1999_02
特許番号
US05874466

反応ノート

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