Dimethylformamide dimethyl acetal → Methyl 4-dimethylaminovinyl-3-nitrobenzoate

HRID 2360615Notes

Reaction equation

HRID 2360615 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([CH:1]=[CH:17][N:18]([CH3:20])[CH3:19])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 81816Methyl 4-methyl-3-nitrobenzoate

Product 1

HCID 894336Methyl 4-dimethylaminovinyl-3-nitrobenzoateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Methyl 4-methyl-3-nitrobenzoate (5 g, 25.6 mmol) was dissolved in DMF (25 mL, 5 vol) and to this was added N,N-dimethylformamide dimethylacetal (4.4 mL, 33.3 mmol). The mixture was allowed to stir at 140° C. for 3 h. The resulting deep red solution was allowed to cool and concentrated under vacuum. The residue was triturated with methanol and filtered. The filtrate was washed with methanol and dried on the sinter to yield 4-(2-dimethylamino-vinyl)-3-nitrobenzoic acid methyl ester (5.2 g, 80%). 1H NMR (300 MHz, DMSO), δ: 2.98 (6H, s, 2×CH3), 3.87 (3H, s, CH3), 5.58 (1H, m, CH), 7.72-7.83 (3H, m, ArH), 8.32 (1H, m, CH).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under vacuum
  3. customThe residue was triturated with methanol
  4. filtrationfiltered
  5. washThe filtrate was washed with methanol
  6. customdried on the sinter

Sources & evidence

ORD record
ord-1cb19ec2226e45799e68b16dfe81e7fa
Source dataset
uspto-grants-2014_04
Patent number
US08686032B2

Reaction notes

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