Dichloromethane → Methyl 3-methoxyiminomethyl-4-nitrobenzoate

HRID 363491노트

반응식

HRID 363491 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 53889174Methyl 3-methoxyiminomethyl-4-nitrobenzoate수율 98.8%

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-262721da2fde40a0b7676296280e478a
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874466

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