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

HRID 1715588ノート

反応式

HRID 1715588 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒2 回HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-29669d8e99414981b736ca281fb49543
出典データセット
uspto-grants-2010_09
特許番号
US07799782B2

反応ノート

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