Hydrochloric Acid → 2-(Aminomethyl)-5-fluorophenol hydrochloride

HRID 1372273노트

반응식

HRID 1372273 반응식
C([O:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[C:11]#[N:12])C1C=CC=CC=1.[ClH:18]>C(O)C.C(OCC)(=O)C.[Pd]>[ClH:18].[OH:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH2:11][NH2:12]

참가 물질

6

반응물 2

HCID 313Hydrochloric AcidHCID 210698282-(Benzyloxy)-4-fluorobenzonitrile

생성물 1

HCID 210698432-(Aminomethyl)-5-fluorophenol hydrochloride수율 74.3%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of intermediate 134, 2-(benzyloxy)-4-fluorobenzonitrile, (9.03 g, 39.7 mmol) in ethanol (100 mL) and ethyl acetate (100 mL) was stirred with 10% palladium on carbon (1.67 g,) and concentrated hydrochloric acid (12 mL, 144 mmol) under a hydrogen atmosphere (60 psi) for four days. The catalyst was removed by filtration through Celite, and the filtrate was concentrated. The crude product was triturated with ether and the resulting solid collected by filtration to give the title compound (5.24 g, 74% yield) as a pale orange solid. 1H NMR (500 MHz, DMSO-D6) δ ppm: 10.81 (1H, s), 8.18 (3H, s), 7.36 (1H, t, J=7.3 Hz), 6.79 (1H, dd, J=10.8, 2.6 Hz), 6.66 (1H, dt, J=8.5, 2.3 Hz), 3.90 (2H, d, J=5.2 Hz).

후처리

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was triturated with ether
  4. filtrationthe resulting solid collected by filtration

출처 및 근거

ORD 기록
ord-8ccc5eb04d7443c085203606fa80cebc
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157447B2

반응 노트

불러오는 중…