Diethyl Malonate → HCID 68637520, compound

HRID 1591716Notes

Reaction equation

HRID 1591716 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[C:5]=1[NH2:11])([O-:3])=[O:2].[C:12](OCC)(=O)[CH2:13][C:14]([O:16]CC)=[O:15]>>[N+:1]([C:4]1[C:5]2[N:11]=[C:12]([CH2:13][C:14]([OH:16])=[O:15])[NH:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 7761Diethyl MalonateHCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 68637520HCID 68637520, compound

Conditions

Temperature
160 °C

Procedure

3-Nitro-benzene-1,2-diamine (5.0 g) was dissolved in diethyl malonate. The reaction was heated at 160° C. oil bath for 48 h. After cooling to rt, flash chromatography of the crude reaction gave (4-nitro-1H-benzoimidazol-2-yl)-acetic acid (4.50 g). MS found: (M+H)+=250.0 (2b) A portion (500 mg) of the above derivative (20a) was dissolved in THF (6 ml) prior to the addition of a solution of LiOH.H2O (100 mg) in water (0.3 ml). A couple drops of MeOH were added until the solution became clear. After 3 h at rt, the reaction was concentrated and freeze-dried to provide (4-nitro-1H-benzoimidazol-2-yl)-acetic acid lithium salt (482 mg). 1H NMR (DMSO, δ ppm, 300 mHz) 3.57 (s, 2H), 7.15 (t, 1H), 7.81 (d, 1H), 7.9 (d, 1H). (2c) Derivative (2b) (50 mg) was incorporated into example (1e) to give the title compound (63 mg). MS found: (M+H)+=468.3.

Workup

  1. temperatureAfter cooling to rt
  2. customflash chromatography of the crude reaction

Sources & evidence

ORD record
ord-9ca13b4995d440dfa96ce46fa6b3b469
Source dataset
uspto-grants-2007_11
Patent number
US07291615B2

Reaction notes

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