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Ammonium formate → 2-Amino-4-(4-propylmorpholin-2-yl)phenol

HRID 2252640
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HRID 2252640 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH3:18])[CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:19])([O-])=O.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([CH:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH3:18])[CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:19]
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참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 574406782-Nitro-4-(4-propylmorpholin-2-yl)phenol

생성물 1

HCID 444439482-Amino-4-(4-propylmorpholin-2-yl)phenol수율 80%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
70 °C

실험 절차

To the nitro from example 36 (95 mg, 0.35 mmol) in ethanol (10 ml) was added 10% palladium on charcoal (50 mg) and ammonium formate (100 mg, XS). The reaction mixture was gently heated to 70° C. and held at this temperature for 1 hour before it was allowed to cool to room temperature. The reaction mixture was then filtered through arbacel and washed with ethanol (20 ml) then dichloromethane (20 ml). The organic washes were combined and concentrated in vacuo to give the title compound as a yellow solid (65 mg, 0.28 mmol, 78%). 1H NMR (CDCl3, 400 MHz) δ: 0.91 (t, 3H), 1.55 (m, 2H), 2.12 (t, 1H), 2.25 (dt, 1H), 2.40 (t, 2H), 2.81-2.92 (dd, 2H), 3.82 (t, 1H), 4.00 (d, 1H), 4.42 (d, 1H), 6.60 (m, 2H), 6.71 (s, 1H). LRMS: m/z 237 (M−H+).

후처리

  1. temperatureto cool to room temperature
  2. filtrationThe reaction mixture was then filtered through arbacel
  3. washwashed with ethanol (20 ml)
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-a79a3bc226334eda9cdc250c79deb57f
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07323462B2

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