Acetic Acid → 4-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine

HRID 1660976노트

반응식

HRID 1660976 반응식
[CH3:1][N:2]([CH3:19])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[C:15]([F:18])([F:17])[F:16].CC(O)=O.O.N>[Fe].CCO>[CH3:19][N:2]([CH3:1])[CH2:3][C:4]#[C:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:15]([F:16])([F:17])[F:18]

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 962WaterHCID 67021317Dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine

생성물 1

HCID 670216344-(3-Dimethylamino-prop-1-ynyl)-3-trifluoromethyl-phenylamine

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of dimethyl-[3-(4-nitro-2-trifluoromethyl-phenyl)-prop-2-ynyl]-amine (2.0 g, 7.4 mmol), iron powder (1.65 g, 29.4 mmol, 4 equiv), AcOH (5 mL), H2O (10 mL), and EtOH (40 mL) is stirred for 30 min at 80° C. The reaction mixture is allowed to cool to rt, basified by addition of a 1 M aqueous solution of NH3, and filtered through Celite. The filtrate is partially concentrated and extracted with EtOAc. The organic phase is washed with brine, dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5) to provide the title compound as a brown oil: ES-MS: 243.0 [M+H]+; single peak at tR=2.49 min (System 1); Rf=0.10 (CH2Cl2/NH3 (2 N in MeOH), 95:5).

후처리

  1. temperatureto cool to rt
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate is partially concentrated
  4. extractionextracted with EtOAc
  5. washThe organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel column chromatography (CH2Cl2/NH3 (2 N in MeOH), 95:5)

출처 및 근거

ORD 기록
ord-06d6aac452524758a13f7cb39adab648
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030311B2

반응 노트

불러오는 중…