4-Methyl-3-nitrobenzoic acid → HCID 73412750, compound

HRID 1808322Notes

Reaction equation

HRID 1808322 reaction equation
[CH3:1][N:2]([CH:4](OC)OC)[CH3:3].[CH3:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20]>CN(C)C=O>[CH3:3][N:2]([CH3:1])[CH:4]=[CH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 73194-Methyl-3-nitrobenzoic acidHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 73412750HCID 73412750, compoundYield 71.79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

DMF-DMA (45.4 g; 2.3 equiv.) was added under a nitrogen atmosphere to a solution of 4-methyl-3-nitrobenzoic acid (30 g; 1 equiv.) in dimethylformamide (150 ml). The resulting reaction mixture was heated for 17 h at 140° C. When the conversion was complete, the DMF was distilled off; 150 ml of methanol were added to the residue, and the mixture was stirred for 2 hours at room temperature and then crystallised overnight at 0-4° C. The resulting solid was filtered out and washed with ice-cold methanol and then with hexane. Drying yielded 4-(2-(dimethylamino)vinyl)-3-nitrobenzoic acid (28 g; 71.79%) in the form of a red solid.

Workup

  1. customThe resulting reaction mixture
  2. distillationthe DMF was distilled off
  3. addition150 ml of methanol were added to the residue
  4. customcrystallised overnight at 0-4° C
  5. filtrationThe resulting solid was filtered out
  6. washwashed with ice-cold methanol
  7. customDrying

Sources & evidence

ORD record
ord-8aaf6b32844b4665b4b9a761d005cdda
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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