Methyl 4-Formylbenzoate → HCID 24827971, compound

HRID 1716839Notes

Reaction equation

HRID 1716839 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH3:13][NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH2:21]>[N+](C1C=CC=CC=1)([O-])=O>[CH3:13][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:21]=[C:1]1[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 15294Methyl 4-FormylbenzoateHCID 78498N-Methyl-o-phenylenediamine

Product 1

HCID 24827971HCID 24827971, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of methyl 4-formylbenzoate (5.0 g, 0.03 mol) and N-methyl-1,2-phenylene diamine (3.7 g, 0.03 mol) in nitrobenzene was heated at 140-150° C. overnight, cooled to room temperature, filtered and the filtercake washed with hexane. The combined filtrates were evaporated to dryness under reduced pressure. The resultant residue was purified by flash chromatography (silica, CHCl3:MeOH 95:5) to afford the title compound in 65% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 8.2 (d, J=8 Hz, 2H), 7.88 (d, J=8 Hz, 2H), 7.83 (s, 1H), 7.37 (m, 1H), 7.35 (m, 2H), 3.96 (s, 3H), 3.9 (s, 3H). LCMS (ESI+) 267 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washthe filtercake washed with hexane
  4. customThe combined filtrates were evaporated to dryness under reduced pressure
  5. customThe resultant residue was purified by flash chromatography (silica, CHCl3:MeOH 95:5)

Sources & evidence

ORD record
ord-1054a1f30cef4626bf5a973980542283
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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