Potassium Hydroxide → (5-nitro-1H-indol-2-yl)methanol

HRID 11160

반응식

HRID 11160 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13](OCC)=[O:14])=[CH:7]2)([O-:3])=[O:2].[OH-].[K+].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CO.O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH2:13][OH:14])=[CH:7]2)([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 14797Potassium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 280312Ethyl 5-nitro-1H-indole-2-carboxylateHCID 4311764Sodium borohydride

생성물 1

HCID 10679279(5-nitro-1H-indol-2-yl)methanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

To a solution of ethyl 5-nitro-1H-indole-2-carboxylate (9.8 g, 42.0 mmol) in methanol (300 mL) was added a solution of 2 M potassium hydroxide (31 mL, 63.0 mmol). The reaction mixture was heated at reflux for 2 h and then the hot solution was filtered, poured onto ice, and acidified. The resultant fine pale brown precipitate was collected by filtration and dried. The crude acid was dissolved in tetrahydrofuran (250 mL) and stirred with 1,1′-carbonyldiimidazole (10.2 g, 63.0 mmol) with gentle warming for 2 h. Water (100 mL) was added and then solid sodium borohydride (7.9 g, 0.21 mol) was added portionwise over 30 min, the reaction mixture was stirred for a further 40 min and then it was quenched with 1 M hydrochloric acid. The tetrahydrofuran was removed at reduced pressure and the residue was dissolved in ethyl acetate, washed, dried, and concentrated to give (5-nitro-1H-indol-2-yl)methanol (903). This material was used without purification in the next step.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationthe hot solution was filtered
  4. additionpoured onto ice
  5. filtrationThe resultant fine pale brown precipitate was collected by filtration
  6. customdried
  7. dissolutionThe crude acid was dissolved in tetrahydrofuran (250 mL)
  8. temperaturewith gentle warming for 2 h
  9. customit was quenched with 1 M hydrochloric acid
  10. customThe tetrahydrofuran was removed at reduced pressure
  11. dissolutionthe residue was dissolved in ethyl acetate
  12. washwashed
  13. customdried
  14. concentrationconcentrated

출처 및 근거

ORD 기록
ord-afddef511fda484ca8479efad51022a6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

연결된 노트

불러오는 중…