Water → 4,5-Dimethoxy-2-[(4-ethoxy-1,4-dioxobutyl)amino]benzoic acid ethyl ester

HRID 498989Notes

Reaction equation

HRID 498989 reaction equation
C([CH:3]([CH2:7][C:8](Cl)=[O:9])[C:4](Cl)=[O:5])C.[CH2:11]([O:13][C:14](=[O:26])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=1[NH2:25])[CH3:12].N1[CH:32]=[CH:31]C=CC=1.[OH2:33]>C1(C)C=CC=CC=1.ClCCl>[CH2:11]([O:13][C:14](=[O:26])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=1[NH:25][C:8](=[O:9])[CH2:7][CH2:3][C:4]([O:5][CH2:31][CH3:32])=[O:33])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 88488Ethyl 2-amino-4,5-dimethoxybenzoateHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 686160054,5-Dimethoxy-2-[(4-ethoxy-1,4-dioxobutyl)amino]benzoic acid ethyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl succinyl chloride (1.284 g, 5.7 mmol) in toluene (15 ml) was added dropwise to a cooled solution of 2-amino-4,5-dimethoxybenzoic acid ethyl ester (1.240 g, 7.4 mmol) and pyridine (0.67 ml) in toluene (1 ml) with stirring under nitrogen. The resulting suspension was stirred for 4 hours at 20° C. and water (13 ml) and dichloromethane then added. The organic phase was washed with hydrochloric acid (10%) and aqueous sodium carbonate solution (5%), dried (sodium sulfate) and evaporated. The residue was crystallised from ethanol to yield the title compound (1.42 g, yield 70%) as colourless crystals, mp 125° C.; 1H-NMR (DMSO-d6, 300 MHz): δ (ppm)=11.26 (br s; 1 H), 8.43 (s; 1H), 7.46 (s; 1H), 4.39 (q, 2H), 4.18 (q, 2H), 3.92 (s, 3H), 3.87 (s; 3H), 2.75 (m; 4H), 1.42 (t, 3H), 1.23 (t, 3H).

Workup

  1. stirringThe resulting suspension was stirred for 4 hours at 20° C.
  2. washThe organic phase was washed with hydrochloric acid (10%) and aqueous sodium carbonate solution (5%)
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customThe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-a4c02956ecbb4240acc5a747e9bb9d3c
Source dataset
uspto-grants-2010_08
Patent number
US07767664B2

Reaction notes

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