Sodium Hydroxide → Methyl 3-amino-2-chlorobenzoate

HRID 51344

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HRID 51344 반응식
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[OH-].[Na+]>Cl.C(O)C>[Cl:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 10751184Methyl 2-chloro-3-nitrobenzoate

생성물 1

HCID 15132848Methyl 3-amino-2-chlorobenzoate수율 50.3%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

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온도
55 °C

실험 절차

A solution of stannous chloride (27.0 g, 137.0 mM) in 55 mL of concentrated hydrochloric acid was slowly added to a solution of methyl 2-chloro-3-nitrobenzoate (6.0 g, 27.9 mM) in 75 mL ethanol at 15-20° C. over 1 hour. The mixture was then heated at 50-60° C. for 15 minutes. The mixture was cooled to room temperature and made alkaline by slow addition of solid sodium hydroxide maintaining a temperature of 30-35° C. The resultant mixture was extracted three times with chloroform. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2.6 g (50%) of methyl 2-chloro-3-aminobenzoate as a yellow oil, identical in all respects to the material derived via catalytic hydrogenation described above.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe resultant mixture was extracted three times with chloroform
  3. washThe extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-87707694df134ea0a0a9a4e45ea82fb8
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713645B1

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