Triethylamine → Methyl 3-(2,3-dihydroxypropyl)amino-2-(3,5-dinitropyridin-2-yl)-2-butenoate

HRID 325886Notes

Reaction equation

HRID 325886 reaction equation
[N+:1]([C:4]1[C:5](F)=[N:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[OH:21][CH:22]([CH2:32][OH:33])[CH2:23][NH:24][C:25]([CH3:31])=[CH:26][C:27]([O:29][CH3:30])=[O:28]>C(O)(C)C>[OH:21][CH:22]([CH2:32][OH:33])[CH2:23][NH:24][C:25]([CH3:31])=[C:26]([C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][N:6]=1)[C:27]([O:29][CH3:30])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12301272Pyridine, 2-fluoro-3,5-dinitro-HCID 71430100Methyl 3-[(2,3-dihydroxypropyl)amino]but-2-enoate

Product 1

HCID 86739362Methyl 3-(2,3-dihydroxypropyl)amino-2-(3,5-dinitropyridin-2-yl)-2-butenoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.5 g (0.0026 m) 3,5-dinitro-2-fluoropyridine (1) and 0.3 g (0.0026 m) triethylamine in 10 ml isopropanol is added 0.48 g (0.0025 m) methyl 3-(2,3-dihydroxypropyl)amino-2-butenoate (2). This solution is stirred at room temperature for two days, concentrated to an oil in vacuo and the residue is chromatographed on silica gel with 8% methanol/chloroform. The material with Rf =0.5 is collected. This reddish brown material is recrystallized from acetonitrile/n-butylchloride, m.p. 128°-9°.

Workup

  1. concentrationconcentrated to an oil in vacuo
  2. customthe residue is chromatographed on silica gel with 8% methanol/chloroform
  3. customThe material with Rf =0.5 is collected
  4. customThis reddish brown material is recrystallized from acetonitrile/n-butylchloride, m.p. 128°-9°

Sources & evidence

ORD record
ord-bb4946710c9e4c179a91eb2074ade5fc
Source dataset
uspto-grants-1984_04
Patent number
US04443458

Reaction notes

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