Sodium Hydroxide → 1-Chloro-3-ethoxyisoquinoline

HRID 1893632노트

반응식

HRID 1893632 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 574451481-Chloro-3-ethoxyisoquinoline수율 40%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
120 °C

실험 절차

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 rt, 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]+.

후처리

  1. temperatureFollowing cooling to rt
  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)

출처 및 근거

ORD 기록
ord-ed83c68ee98e4c88ba333c80fa3a1058
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513186B2

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