Chlorobenzene → HCID 18800935, compound

HRID 1885547Notes

Reaction equation

HRID 1885547 reaction equation
CN(C[C:5]1[C:9]2[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][CH:6]=1)C.[N+:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])([O-:19])=[O:18].Cl[C:27]1C=CC=CC=1>>[N+:14]([C:10]1[CH:11]=[CH:12][CH:13]=[C:8]2[C:9]=1[CH:5]=[C:6]([CH2:27][CH:20]([N+:17]([O-:19])=[O:18])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[NH:7]2)([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 7964ChlorobenzeneHCID 69379Ethyl nitroacetateHCID 2514534-NITROGRAMINE

Product 1

HCID 18800935HCID 18800935, compound

Procedure

A solution of 60 g of 4-nitrogramine [J. B. Hester, J. Org. Chem., 29, 1158 (1964)] and 54 g of ethyl nitroacetate in 1.2 L of chlorobenzene was heated at 100° C. for 1.5 h. After cooling the mixture was filtered, washed with cold methylene chloride and dried in vacuo to afford 58.9 g of ethyl 3-(4-nitro-2-indolyl)-2-nitropropionate as a yellow solid: mp 159°-160.5° C. Another 11 g may be recovered from the filtrate by dilution with hexane, preparative liquid chromatography [silica; methylene chloride/ethyl acetate (90:10)] and recrystalization from methanol. The structure was confirmed by NMR.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. washwashed with cold methylene chloride
  4. customdried in vacuo

Sources & evidence

ORD record
ord-58c9ae7d6e4a49efb2ee778dd435593a
Source dataset
uspto-grants-1992_09
Patent number
US05145842

Reaction notes

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