Hydrochloric Acid → 2-(Aminomethyl)-5-chloro-4-nitrobenzenamine

HRID 508870노트

반응식

HRID 508870 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4]([NH2:6])=O.Cl.[OH-].[Na+]>C1COCC1>[NH2:6][CH2:4][C:3]1[CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]([Cl:11])=[CH:10][C:2]=1[NH2:1]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10751185HCID 10751185, 화합물

생성물 1

HCID 900190742-(Aminomethyl)-5-chloro-4-nitrobenzenamine수율 72.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-amino-4-chloro-5-nitrobenzamide (3.0 g, 13.7 mmol) in dry THF (50 mL), borane dimethyl suphide complex (1.56 g, 20.6 mmol) was added at RT and the reaction mass was refluxed for 24 h. The reaction mass was cooled to RT and dilute HCl was added till it became acidic. Further, the reaction mixture was stirred for 1 h and then the reaction mixture was basified with dilute NaOH and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 2.0 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 3.58 (s, 2H), 6.72 (br s, 3H), 8.04 (br s, 1H); MS (m/z): 200.28 (M−H).

후처리

  1. temperaturethe reaction mass was refluxed for 24 h
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-651c41444aba452c8d2402bb907a6b7b
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096545B2

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