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

HRID 1660976ノート

反応式

HRID 1660976 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-06d6aac452524758a13f7cb39adab648
出典データセット
uspto-grants-2011_10
特許番号
US08030311B2

反応ノート

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