Hydrochloric Acid → 4-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid

HRID 216581노트

반응식

HRID 216581 반응식
[OH-].[NH4+:2].[Cl:3][C:4]1[C:5]([F:17])=[C:6]([CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[C:12]=1F)[C:7]([OH:9])=[O:8].Cl>O>[NH2:2][C:12]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([F:17])[C:4]=1[Cl:3]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14923Ammonium Hydroxide2회HCID 155499183-Chloro-2,4-difluoro-5-nitrobenzoic acid

생성물 1

HCID 211141824-Amino-3-chloro-2-fluoro-5-nitro-benzoic acid수율 85.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Ammonium hydroxide solution (6.88 g, −30% in water, 58.9 mmol) is added to a solution of 3-chloro-2,4-difluoro-5-nitro-benzoic acid 2a (3.5 g, 14.7 mmol) in water (16 mL) at 0° C. with stirring. Upon completion of the ammonium hydroxide addition the reaction mixture is warmed to room temperature. After 5 hours the reaction mixture is cooled to 0° C. and concentrated HCl is carefully added until the pH of the reaction mixture is near zero. The solid is collected by filtration and washed with water and diethyl ether. The solids are transferred to a round bottom flask as a solution in MeOH and EtOAc and concentrated under reduced pressure to give 2.96 g of a yellow solid. The filtrate is partitioned between diethyl ether and water and the organic layer is washed with brine. The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure to give 0.65 g of product. Recovered a total of 3.61 g (104%) of pure desired product that is carried forward without further purification.

후처리

  1. temperatureAfter 5 hours the reaction mixture is cooled to 0° C.
  2. filtrationThe solid is collected by filtration
  3. washwashed with water and diethyl ether
  4. customThe solids are transferred to a round bottom flask as a solution in MeOH
  5. concentrationEtOAc and concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4ec2d07d46af4355981092608d4708d1
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193230B2

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