Triethylamine → HCID 70029470, compound

HRID 2270797Notes

Reaction equation

HRID 2270797 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:20]=[CH:19][C:8]([C:9]([O:11]N2C(=O)CCC2=O)=O)=[CH:7][C:6]=1[CH3:21])=[O:4].[OH:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].C(N(CC)CC)C>CN(C)C=O>[OH:22][C:23]1[CH:24]=[C:25]([CH2:26][NH:27][C:9]([C:8]2[CH:19]=[CH:20][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:6]([CH3:21])[CH:7]=2)=[O:11])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7358943-(Aminomethyl)phenolHCID 20714746HCID 20714746, compound

Product 1

HCID 70029470HCID 70029470, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[[4-(methoxycarbonyl)-3-methylbenzoyl]oxy]-2,5-pyrrolidinedione (Example 6; 6.00 g, 20.6 mmol), 3-hydroxybenzylamine (2.92 g, 23.7 mmol) and triethylamine (2.61 g, 25.8 mmol) in N,N-dimethylformamide (100 mL) was stirred at room temperature overnight. The solvent was evaporated (<0.5 mm Hg, 40° C.) and ethyl acetate (200 mL) was added. The solution was washed with 0.5N hydrochloric acid (200 mL), brine (200 mL), saturated sodium bicarbonate solution (2×150 mL) and brine (200 mL). Each aqueous layer was back-extracted in turn with ethyl acetate (100 mL). The combined organic layers were dried (MgSO4), filtered, and evaporated to give 4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]-2-methylbenzoic acid, methyl ester (5.63 g, 91%) as an orange liquid that solidified on standing, mp 100-103° C.

Workup

  1. customThe solvent was evaporated (<0.5 mm Hg, 40° C.) and ethyl acetate (200 mL)
  2. additionwas added
  3. washThe solution was washed with 0.5N hydrochloric acid (200 mL), brine (200 mL), saturated sodium bicarbonate solution (2×150 mL) and brine (200 mL)
  4. extractionEach aqueous layer was back-extracted in turn with ethyl acetate (100 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-95e810b317914d48b1b7eba660cb1a4e
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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