4-Nitro-1H-indole → Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

HRID 551077

반응식

HRID 551077 반응식
P(Cl)(Cl)(OP(Cl)(Cl)=O)=O.[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH:15]=[CH:16][NH:17]2)([O-:12])=[O:11].[C:22]([O:26]N1CCCC1C)(=[O:25])[CH:23]=[O:24].[C:33]([O-])(O)=O.[Na+]>CO>[N+:10]([C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[C:15]([C:23](=[O:24])[C:22]([O:26][CH3:33])=[O:25])=[CH:16][NH:17]2)([O-:12])=[O:11]

참가 물질

6

반응물 4

HCID 1457664-Nitro-1H-indoleHCID 516892Sodium BicarbonateHCID 4432411Diphosphoryl tetrachlorideHCID 86629729HCID 86629729, 화합물

생성물 1

HCID 10243717Methyl (4-nitro-1H-indol-3-yl)(oxo)acetate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Diphosphoryl chloride (0.938 mL, 6.80 mmol) was added dropwise to a solution of 4-nitroindole (1.00 g, 6.17 mmol) and methylpyrrolidinyl glyoxylate (Downie et al., Tetrahedron, 1993, 49, 4015-4034) (1.10 g, 6.80 mmol) at 0° C. and the mixture was allowed to warm to ambient temperature over 3 h. MeOH, then saturated aqueous NaHCO3 were added to the reaction at 0° C. and the solution was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo until crystals formed. The crystals were collected by vacuum filtration and two more crops were isolated from the filtrate to give the title compound. MS: m/z=249 (M+1).

후처리

  1. extractionthe solution was extracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo until crystals
  5. customformed
  6. filtrationThe crystals were collected by vacuum filtration and two more crops
  7. customwere isolated from the filtrate

출처 및 근거

ORD 기록
ord-e7bdc9ce3d3f4d53b12434c9a30abf3e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947677B2

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