4-Anilino-3-nitrobenzoic acid → 3-Amino-4-phenylamino-benzoic acid

HRID 74146

반응식

HRID 74146 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:7]([OH:9])=[O:8])([O-])=O.[H][H]>[Pd].O1CCCC1>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:7]([OH:9])=[O:8]

참가 물질

5

반응물 2

HCID 38243664-Anilino-3-nitrobenzoic acidHCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 7738213-Amino-4-phenylamino-benzoic acid수율 95.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8028Tetrahydrofuran용매

실험 절차

A 3-neck flask was charged with 3-nitro-4-phenylaminobenzoic acid (see Synthesis Example 1-1) (1.67 g, 6.70 mmol), palladium/carbon (Pd:10%, 0.170 g), and tetrahydrofuran (34 mL), the atmosphere was replaced with hydrogen using three cycles of vacuum/hydrogen purge, and this was stirred at room temperature for 2.5 hours. After substituting in nitrogen, distilled water (20 mL) was added and this was stirred for 10 minutes, insoluble material was filtered off through a Celite layer (20 mm thickness), and this same layer was further washed with tetrahydrofuran (20 mL, 3 times). The filtrate and the wash solutions were combined, and the solvent was distilled off under reduced pressure. This was successively extracted with ethyl acetate (approx. 50 mL, 4 times), washed with distilled water (30 mL), and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and further drying under reduced pressure yielded the title compound (1.45 g, 95.3% yield) as a pale yellow solid.

후처리

  1. custompurge
  2. distillationdistilled water (20 mL)
  3. additionwas added
  4. stirringthis was stirred for 10 minutes
  5. filtrationinsoluble material was filtered off through a Celite layer (20 mm thickness)
  6. washthis same layer was further washed with tetrahydrofuran (20 mL, 3 times)
  7. distillationthe solvent was distilled off under reduced pressure
  8. extractionThis was successively extracted with ethyl acetate (approx. 50 mL, 4 times)
  9. washwashed with distilled water (30 mL)
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customfurther drying under reduced pressure

출처 및 근거

ORD 기록
ord-3f6cded859c546208933eab05023e6dc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829035B2

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