Dimethylformamide → ethyl 3-methyl-4-nitrobenzoate

HRID 962942Notes

Reaction equation

HRID 962942 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].CN(C)C=O.C(=O)(O)[O-].[Na+].I[CH2:25][CH3:26]>O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH2:25][CH3:26])=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 183703-Methyl-4-nitrobenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2796918ethyl 3-methyl-4-nitrobenzoateYield 91.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-methyl-4-nitrobenzoic acid (1) (362.3 g, 2.0 mol), N,N-dimethylformamide (2000 mL), sodium bicarbonate (200 g, 2.38 mol) and iodoethane (623.9 g, 4.0 mol) was stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature and poured into water (2000 mL. The resulting solid was collected by filtration, washed with water and dried. The solid was washed further with hexane and dried to provide the title product (382.1 g, 91%) as an off-white solid: mp 51°-52.5° C.; 1H NMR (CDCl3) δ 8.04-7.98 (m, 3H), 4.42 (q, 2H), 2.63 (s, 3H), 1.42 (t, 3H); Mass spectrum (NH3 --CI) m/z 210 (100%, M+H+).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. washThe solid was washed further with hexane
  6. customdried

Sources & evidence

ORD record
ord-767328e277a949d89df8211e8f23f8dd
Source dataset
uspto-grants-1998_06
Patent number
US05760028

Reaction notes

Loading…