Ammonium Chloride → 2-(4-Amino-3-methylphenoxy)-5-fluorobenzonitrile

HRID 1715588노트

반응식

HRID 1715588 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[C:13]([CH3:20])[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH4+].[Cl-]>[Zn].CO.C1COCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:9][C:6]=2[C:7]#[N:8])=[CH:12][C:13]=1[CH3:20]

참가 물질

5

반응물 2

HCID 25517Ammonium ChlorideHCID 574187545-Fluoro-2-(3-methyl-4-nitrophenoxy)-benzonitrile

생성물 1

HCID 574187552-(4-Amino-3-methylphenoxy)-5-fluorobenzonitrile

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 21899815MeOH tetrahydrofuran용매

실험 절차

Intermediate (24t) (14.3 g, mmol) and zinc dust (17.2 g, 263 mmol) were suspended in mixed solvent of MeOH/THF (1:1, 125 mL) and saturated NH4Cl (125 mL) was added. The reaction mixture became warm. There was an obvious change in the zinc suspension. The reaction was finished in 10 minutes. The reaction mixture was filtered through a silica plug and diluted with EtOAc and saturated NaHCO3. The layers were separated and the combined organics dried over MgSO4 and concentrated under reduced pressure. The crude residue (25t) was pure enough on NMR spectra. 1HNMR (400 MHz, d6-DMSO) δ 7.83 (dd, J=8.5, 3.1 Hz, 1H), 7.47 (td, J=8.9, 3.1 Hz, 1H), 6.83-6.77 (m, 2H), 6.74 (dd, J=8.6, 2.3 Hz, 1H), 6.66 (d, J=8.6 Hz, 1H), 4.88 (s, 1H), 2.06 (s, 3H) ppm.

후처리

  1. additionwas added
  2. temperatureThe reaction mixture became warm
  3. filtrationThe reaction mixture was filtered through a silica plug
  4. additiondiluted with EtOAc and saturated NaHCO3
  5. customThe layers were separated
  6. dry with materialthe combined organics dried over MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-29669d8e99414981b736ca281fb49543
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07799782B2

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