5-Nitro-1-benzothiophene → Benzo(b)thiophen-5-amine

HRID 507518

반응식

HRID 507518 반응식
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-])=O>[Pd].C(O)C>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[C:4]([NH2:1])[CH:12]=[CH:11][C:7]1=2

참가 물질

4

반응물 1

HCID 124140845-Nitro-1-benzothiophene

생성물 1

HCID 288032Benzo(b)thiophen-5-amine수율 101.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of 5-nitrobenzo[b]thiophene (3.09 g, 17.0 mmol) and 10% palladium on carbon (Aldrich, cat. No. 20,569-9) (150 mg) in ethanol (90 mL) was shaken in a Parr flask under a hydrogen atmosphere of 3 bar. After 16 h the catalyst was filtered off over a celite pad and washed with ethanol (2×30 mL). The filtrate was evaporated in vacuo to yield benzo[b]thiophen-5-amine (2.57 g, 100%) as a dark purple amorphous solid. 1H NMR δ (CDCl3, 400 MHz) 3.70 (br. s., 2H), 6.78 (dd, J=8.61, 1.96 Hz, 1H), 7.10 (d, J=2.35 Hz, 1H), 7.14 (d, J=5.09 Hz, 1H), 7.38 (d, J=5.48 Hz, 1H), 7.63 (d, J=8.61 Hz, 1H)

후처리

  1. filtrationAfter 16 h the catalyst was filtered off over a celite pad
  2. washwashed with ethanol (2×30 mL)
  3. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-e3cf1d45f6ba40ce9ec63dba049fe2ca
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786132B2

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