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

HRID 2353300Notes

Reaction equation

HRID 2353300 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, 6.8 mol) was added dropwise to a solution of 4-nitroindole (1 g, 6.2 mol) and methylpyrrolidinyl glyoxylate (Downie et al., Tetrahedron, 1993, 49, 4015-4034) (1.1 g, 6.8 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-2d0e6ff288ed4a29adce41bf793e9c36
Source dataset
uspto-grants-2010_07
Patent number
US07750010B2

Reaction notes

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