Sodium Hydroxide → 3-Amino-2-hydroxybenzonitrile

HRID 612690

反応式

HRID 612690 の反応式
[C:1]([C:3]1[C:8]([OH:9])=[C:7]([N+:10]([O-])=O)[CH:6]=[CH:5][CH:4]=1)#[N:2].[Sn](Cl)Cl.[OH-].[Na+]>C(O)(=O)C>[NH2:10][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([C:1]#[N:2])[C:8]=1[OH:9]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 124686862-Hydroxy-3-nitrobenzonitrile

生成物 1

HCID 124686813-Amino-2-hydroxybenzonitrile収率 272.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6-cyano-2-nitrophenol(600 mg, 1.0 mmol) and tin (II) chloride (3.2 g, 14.4 mmol) in acetic acid(50 mL) was heated at 80° C. under argon. After 2 hours, the starting material has disappeared and the solution was allowed to cool down and then poured into ice. The pH was made slightly basic (pH7-8), by addition of solid NaOH, before being extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2Cl2) gave the desired product(365 mg, 75%). 1H NMR (CD3OD): δ 6.92 (d, 1H), 6.85-6.69 (m, 2H).

後処理

  1. temperatureto cool down
  2. additionpoured into ice
  3. extractionbefore being extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-2f04598f40eb423eb661e123d9d7fc62
出典データセット
uspto-grants-1999_12
特許番号
US06005008

関連ノート

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