Dimethylamine → HCID 59352996, compound

HRID 1914705Notes

Reaction equation

HRID 1914705 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6](O)=[O:7].[CH3:15][NH:16][CH3:17]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[C:6]([N:16]([CH3:17])[CH3:15])=[O:7]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 53002123-Methoxy-5-nitrobenzoic acid

Product 1

HCID 59352996HCID 59352996, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Methoxy-5-nitrobenzoic acid (1 g; 5.1 mmol; 1 eq) is preactivated with n-(3-dimethyl aminopropyl)-n′-ethylcarbodiimide hydrochloride (1.2 g; 6.1 mmol; 1.2 eq) in DCM (30 mL) for 10 mM. Dimethylamine (343 mg; 7.6 mmol; 1.5 eq) is then added and the reaction mixture stirred overnight. After quenching the reaction mixture with water, the organic phase is washed with water and citric acid (5%) and dried over MgSO4. The solvent is evaporated to dryness according 1.1 g (97%) of the title compound as a red oil. 1H NMR (DMSO-d5) δ 7.83-7.77 (m, 1H), 7.74-7.68 (m, 1H), 7.27-7.21 (m, 1H), 3.87 (s, 3H), 3.08 (s, 3H), 2.96 (s, 3H). HPLC (max plot) 91.9%; Rt 2.52 min.

Workup

  1. customAfter quenching the reaction mixture with water
  2. washthe organic phase is washed with water and citric acid (5%)
  3. dry with materialdried over MgSO4
  4. customThe solvent is evaporated to dryness

Sources & evidence

ORD record
ord-5c13182725254262892849be7b3c163f
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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