2-Chloro-3-nitrobenzoic acid → N-methyl-N-hydroxy-2-chloro-3-nitrobenzamide

HRID 1421848

반응식

HRID 1421848 반응식
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)(Cl)=O.Cl.[CH3:19][NH:20][OH:21].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.O.CCOCC>[CH3:19][N:20]([OH:21])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]=1[Cl:1]

참가 물질

8

반응물 4

HCID 198702-Chloro-3-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 77906N-methylhydroxylamine hydrochlorideHCID 516892Sodium Bicarbonate

생성물 1

HCID 18706122N-methyl-N-hydroxy-2-chloro-3-nitrobenzamide수율 89.5%

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

To a stirred solution of 2-chloro-3-nitrobenzoic acid (6.0 grams, 0.031 mole) in toluene (100 mL) was added thionyl chloride (6.8 mL, 0.092 mole). Upon completion of addition, the reaction mixture was heated to reflux where it stirred for four hours. After this time, the reaction mixture was filtered and concentrated. The concentrate was taken up in ether and added dropwise to an ice-cold solution of N-methylhydroxylamine hydrochloride (2.6 g, 0.031 mole), sodium bicarbonate (5.5 g, 0.065 mole), water (20 mL), and ether (160 mL). Upon completion of addition, the reaction mixture was stirred for one hour. After this time, the reaction mixture was diluted with water and the ether layer was separated. The aqueous layer was extracted twice with ether. The combined ether layer and extracts were dried over magnesium sulfate and concentrated to provide 6.4 grams of N-methyl-N-hydroxy-2-chloro-3-nitrobenzamide. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux where it
  4. filtrationAfter this time, the reaction mixture was filtered
  5. concentrationconcentrated
  6. additionUpon completion of addition
  7. stirringthe reaction mixture was stirred for one hour
  8. customthe ether layer was separated
  9. extractionThe aqueous layer was extracted twice with ether
  10. dry with materialThe combined ether layer and extracts were dried over magnesium sulfate
  11. concentrationconcentrated

출처 및 근거

ORD 기록
ord-508616ff3d344431965cb4b8d09d056a
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06080702

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