Ethanol → 4-[(3,4-Dichloro-6-fluorophenyl)amino]-6-aminoquinazoline

HRID 346414

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HRID 346414 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([N+:21]([O-])=O)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:5]([F:9])=[CH:6][C:7]=1[Cl:8].C(O)C.C(O)(C)C.O.NN>O.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([NH2:21])[CH:19]=3)[N:14]=[CH:13][N:12]=2)[C:5]([F:9])=[CH:6][C:7]=1[Cl:8]

참가 물질

7

반응물 4

HCID 702EthanolHCID 3776IsopropanolHCID 24654Hydrazine hydrate (1:1)2회HCID 154809984-[(3,4-Dichloro-6-fluorophenyl)amino]-6-nitroquinazoline

생성물 1

HCID 115443254-[(3,4-Dichloro-6-fluorophenyl)amino]-6-aminoquinazoline

시약·촉매·용매 2

HCID 935Nickel촉매2회HCID 962Water용매

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온도
95 °C

실험 절차

A solution of 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline (709 mg, 2.076 mmol) in 140 ml of 1:9:10 water:ethanol:iso-propylalcohol was heated to reflux temperature (95° C.). Additional 60 ml of the solvents mixture was added until complete dissolution. The reaction mixture was then cooled to 65° C., and 200 μl hydrazine hydrate (4.12 mmol) and 0.5 ml Raney®Nickel (in water) were added subsequently thereto. The resulting mixture was heated up to 80–85° C., additional 0.5 ml Raney®Nickel and 50 μl of hydrazine hydrate (1.03 mmol) were added, and gentle reflux was maintained for about 15–20 minutes. Filtration and evaporation gave 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline (compound 2) in 83% yield. m.p.=265° C.; MS (m/z): 323.4, 325.4 (M+); Anal. calcd.: C, 52.9; H, 2.78; N, 17.33. Found: C, 52.19; H, 2.99; N, 17.14. HPLC analysis. C-18 column, 55% acetate buffer, PH=3.8/45% acetonitrile, flow=1 ml/min; r.t=6.6 minutes.

후처리

  1. temperatureThe reaction mixture was then cooled to 65° C.
  2. temperatureThe resulting mixture was heated up to 80–85° C.
  3. temperaturegentle reflux
  4. temperaturewas maintained for about 15–20 minutes
  5. filtrationFiltration and evaporation

출처 및 근거

ORD 기록
ord-27cadef5d46d497385dc647efc143730
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07172749B2

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