Sodium Hydroxide → 3,4-Diaminobenzonitrile

HRID 54306

반응식

HRID 54306 반응식
[Cl-].[Cl-].[Ca+2].FC1C=CC(N)=C(N)C=1.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][C:15]=1[N+:22]([O-])=O.FC1C(N)=C(N)C=CC=1.[OH-].[Na+]>CCO.Cl.[Zn].O>[NH2:22][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:14]=1[NH2:13])[C:18]#[N:19]

참가 물질

10

반응물 5

HCID 14798Sodium HydroxideHCID 1645844-Fluorobenzene-1,2-diamineHCID 5959014-Amino-3-nitrobenzonitrileHCID 27828353-Fluorobenzene-1,2-diamineHCID 5284359Calcium Chloride

생성물 1

HCID 7372853,4-Diaminobenzonitrile

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 313Hydrochloric Acid용매HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

3,4-Diaminobenzonitrile was prepared using an adaptation of the method of Tsuji et al. (Tsuji, Y. et al., J. Org. Chem. 55:580 (1990)). Zn powder (2.51 g, 38.3 mmol), CaCl2 (251 mg), H2O (3.0 mL) and 9.0 mL EtOH were combined and brought to reflux as described for 4-fluoro-1,2-diaminobenzene (Example 10) and to this mixture was added slowly dropwise a solution of 4-amino-3-nitrobenzonitrile (500 mg, 3.06 mmol) in 20 mL EtOH. Analysis and workup were described for 3-fluoro-1,2-diaminobenzene except that the reaction residue was dissolved in 20 mL 1N HCl . This solution was then made basic by the addition of 20 mL 1.5M NaOH. A precipitate separated as fine tan needles which were collected by vacuum filtration, rinsed with cold H2O and dried in a vacuum desiccator (0.5 torr, 25° C.) over CaSO4 to yield 275 mg (67%) of tan crystals. 1H NMR (CDCl3) δ3.42 (br, s, 2H, NH2), 3.86 (br s, 2H, NH2), 6.70 (d, J=8, 1H, ArH), 6.96 (d, J=1, 1H, ArH), 7.06 (dd, J=8, J=1, 1H, ArH).

후처리

  1. temperatureto reflux
  2. customA precipitate separated as fine tan needles which
  3. filtrationwere collected by vacuum filtration
  4. washrinsed with cold H2O
  5. dry with materialdried in a vacuum desiccator (0.5 torr, 25° C.) over CaSO4

출처 및 근거

ORD 기록
ord-26fd211bcc74466c80c0920d70edfbe4
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622952

연결된 노트

불러오는 중…