Sodium Hydroxide → (3-Chloroisoquinolin-8-yl)methanol

HRID 920247노트

반응식

HRID 920247 반응식
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12](O)=[O:13].B.C1COCC1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[CH2:12][OH:13]

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 895248833-Chloroisoquinoline-8-carboxylic acid

생성물 1

HCID 89524955(3-Chloroisoquinolin-8-yl)methanol

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of 3-chloroisoquinoline-8-carboxylic acid (0.5 g, 1.803 mmol) in THF (18.03 ml) at 0° C. was treated with BH3.THF (5.41 ml, 5.41 mmol). After stirring for 2 hours at 0° C., 1N NaOH was added. The reaction was stirred for 30 minutes then diluted with EtOAc and the layers were separated. Aqueous layer was washed with EtOAc three times. All combined organic layers were washed with brine, then dried with sodium sulfate. Filtered and concentrated in vacuo. Purified by silica gel chromatography (0-100% EtOAc in hexane) to yield (3-chloroisoquinolin-8-yl)methanol.

후처리

  1. stirringThe reaction was stirred for 30 minutes
  2. customthe layers were separated
  3. washAqueous layer was washed with EtOAc three times
  4. washAll combined organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. filtrationFiltered
  7. concentrationconcentrated in vacuo
  8. customPurified by silica gel chromatography (0-100% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-58fbf893efed4b78941cd3312d112788
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273040B2

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