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

HRID 1094095Notes

Reaction equation

HRID 1094095 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2fe46e1b5cc6467d874273baab9beafb
Source dataset
uspto-grants-2012_03
Patent number
US08133891B2

Reaction notes

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