Hydrochloric Acid → 3-(Aminomethyl)benzoic acid hydrochloride

HRID 1682526노트

반응식

HRID 1682526 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].C(O)(C)C.[ClH:16].CCOCC>C1COCC1.[Pt](=O)=O>[ClH:16].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 3776IsopropanolHCID 158753-Cyanobenzoic acid

생성물 1

HCID 162187723-(Aminomethyl)benzoic acid hydrochloride수율 82%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8028Tetrahydrofuran용매

실험 절차

3-cyanobenzoic acid (5.88 g, 40 mmol) was suspended in 50 mL THF and the mixture was warmed up with stirring. After all solid went into solution, 50 mL isopropanol was added and the solution was allowed to cool to room temperature. To it was added 4.2 mL precooled concentrated HCl followed by 300 mg platinum(IV) oxide. The mixture was hydrogenated at 55 psi overnight. Ether (50 mL) was added, and the precipitate was filtered, washed with ether and dissolved in methanol. The catalyst was filtered off and the solvent was removed under reduced pressure to give 6.2 g (82%) product. 1H-NMR (DMSO-d6): δ=4.08 (d, 2H); 7.53 (t, 1H); 7.80 (d, 1H); 7.94 (d, 1H); 8.10 (s, 1H); 8.65 (s, 3H).

후처리

  1. temperaturethe mixture was warmed up
  2. additionwas added
  3. additionTo it was added 4.2 mL
  4. customwas hydrogenated at 55 psi overnight
  5. filtrationthe precipitate was filtered
  6. washwashed with ether
  7. dissolutiondissolved in methanol
  8. filtrationThe catalyst was filtered off
  9. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-c6b191077f29469997c31d5ba11397c7
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05635477

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