Methyl 4-nitrobutyrate → HCID 54562479, compound

HRID 1600883Notes

Reaction equation

HRID 1600883 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=O)=[CH:2]1.C([O-])(=O)C.[NH4+].[N+:17]([CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])([O-:19])=[O:18]>C1COCC1>[CH3:26][O:25][C:23](=[O:24])[CH2:22][CH2:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][CH:2]=1

Participants

5

Reactant 3

HCID 25604Methyl 4-nitrobutyrateHCID 517165Ammonium Acetate2×HCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 54562479HCID 54562479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.47 g (10 mM) of 1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (J. Am. Chem. Soc., 1955, 77, 457-459), 77 mg (10 mM) of ammonium acetate and 2.55 mL (20 mM) of methyl 4-nitrobutyrate (Aldrich) was refluxed in 10 mL of THF for 1 hour. An additional 500 mg of ammonium acetate was added and the mixture refluxed for an additional 3 hours. The reaction was cooled to room temperature, the solvent evaporated, and the residue chromatographed on silica using ethyl acetate as the elutant. Appropriate fractions were combined to yield 410 mg of the desired product as an oil. NMR (D6DMSO) δ12.80 (s, 1H), 8.42 (s, 1H), 8.37 (m, 2H), 8.18 (s, 1H), 7.25 (m, 1H), 3.62 (s, 3H), 3.25 (t, 2H), 2.68 (t, 2H). 13C NMR (D6DMSO) 172.4, 148.7, 144.5, 144.4, 130.0, 127.3, 126.9, 119.9, 117.3, 106.1, 51.6, 30.5, 23.6. Mass Spectrum: m/e=276 (P+1).

Workup

  1. temperaturethe mixture refluxed for an additional 3 hours
  2. customthe solvent evaporated
  3. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-c4b5b08185ae43038c072489092fae62
Source dataset
uspto-grants-1999_11
Patent number
US05977131

Reaction notes

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