Dimethyl 4-aminoisophthalate → Dimethyl-4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalate

HRID 236985Notes

Reaction equation

HRID 236985 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([NH2:14])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[CH2:16]([O:18][C:19]1[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])[CH3:17]>O1CCOCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[CH:12][C:11]([NH:14][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][CH:26]=[C:27]([O:28][CH3:29])[C:19]=2[O:18][CH2:16][CH3:17])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 2

HCID 11095854Dimethyl 4-aminoisophthalateHCID 213147772-Ethoxy-3-methoxybenzoyl chloride

Product 1

HCID 12528358Dimethyl-4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalateYield 97.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

Dimethyl- 4-amino-isophthalate (5 g) in 50 ml of dioxane and 10 ml of anhydrous pyridine is treated with 7.5 g of 2-ethoxy-3-methoxybenzoyl chloride at room temperature, overnight. After dilution with water, the precipitate is collected, dissolved in ethyl acetate, and washed with 5% NaHCO3 and then with water. After evaporation to dryness under vacuum, the material is crystallized from isopropyl ether, yielding dimethyl- 4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalate (9 g; m.p. 113°-115° C.), which is dissolved in 80 ml of dioxane and treated with 70 ml of 1N NaOH at room temperature for 4 hours. After acidification with diluted HCl, the precipitate is collected under vacuum and washed with water until neutral. The yield is 7.4 g of 4-(2'-ethoxy-3'-methoxy-benzoylamino)-isophthalic acid (m.p.=244°-246° C.), which are treated with 10 ml of acetic anhydride at the reflux temperature for 10'.

Workup

  1. customAfter dilution with water, the precipitate is collected
  2. dissolutiondissolved in ethyl acetate
  3. washwashed with 5% NaHCO3
  4. customAfter evaporation to dryness under vacuum
  5. customthe material is crystallized from isopropyl ether

Sources & evidence

ORD record
ord-e42a292bea5343308bccdf6f0172aa9d
Source dataset
uspto-grants-1979_06
Patent number
US04159330

Reaction notes

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