Sodium Hydroxide → 1-Chloro-3-ethoxyisoquinoline

HRID 2405781ノート

反応式

HRID 2405781 の反応式
[CH2:1]([O:3][C:4]1[N+:5]([O-])=[CH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2].[OH-].[Na+].O=P(Cl)(Cl)[Cl:19]>C(Cl)(Cl)Cl>[Cl:19][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[C:4]([O:3][CH2:1][CH3:2])[N:5]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 686175523-ethoxyisoquinoline N-oxide

生成物 1

HCID 574451481-Chloro-3-ethoxyisoquinoline収率 40%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
120 °C

実験手順

3-Ethoxyisoquinoline N-oxide (1.15 g, 6.1 mmol) was taken up in POCl3 (5 mL) at rt and then heated to 120° C. under an atmosphere of Ar for 2 h. Following cooling to it, the reaction was diluted with CHCl3 and poured into icewater (20 mL) and the resulting solution was placed in an ice bath and treated with 10M NaOH until pH 10 with vigorous stirring. Following extraction with CHCl3, the combined organics were washed with brine and dried over anhydrous MgSO4. Following concentration in vacuo, purification on SiO2 (3-15% EtOAc/hex) afforded 0.51 g (40%) of 1-chloro-3-ethoxyisoquinoline. LCMS found 208.1 [M+H]+.

後処理

  1. temperatureFollowing cooling to it
  2. additionpoured into icewater (20 mL)
  3. customthe resulting solution was placed in an ice bath
  4. extractionextraction with CHCl3
  5. washthe combined organics were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentration
  8. customin vacuo, purification on SiO2 (3-15% EtOAc/hex)

出典と根拠

ORDレコード
ord-9993585a9bd84d6e9d345cc39d0c2d35
出典データセット
uspto-grants-2014_08
特許番号
US08809267B2

反応ノート

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