Diisopropylethylamine → HCID 22556078, compound

HRID 985178Notes

Reaction equation

HRID 985178 reaction equation
[ClH:1].[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([OH:14])[CH:5]=1.C(N(C(C)C)CC)(C)C.Br[CH2:25][C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([OH:36])[CH:27]=1>CN(C)C=O.Cl.C(OCC)(=O)C>[ClH:1].[OH:14][C:6]1[CH:5]=[C:4]([CH2:3][NH:2][CH2:25][C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:28]([OH:36])[CH:27]=2)[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 22556059Methyl 4-(bromomethyl)-2-hydroxybenzoateHCID 22556073Methyl 4-aminomethylsalicylate hydrochloride

Product 1

HCID 22556078HCID 22556078, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolved methyl 4-aminomethyl-2-hydroxybenzoate hydrochloride (13.07 g, 60.1 mmole) and diisopropylethylamine (28.0 mL, 292 mmole) in 225 mL of N,N-dimethyl-formamide by heating slightly until a solution was obtained. Allowed the solution to cool to room temperature and added methyl 4-bromomethyl-2-hydroxybenzoate (9.81 g, 40.0 mmole). The reaction was stirred for 1 day at room temperature. The solution was diluted with 200 mL of 1N HCl and 250 mL of ethyl acetate and allowed to cool to room temperature. Precipitate was collected by filtration, washed with ethyl acetate and dried in vacuo under a under high vacuum. Obtained 11.32 grams (74% yield) of product as a white solid.

Workup

  1. temperatureby heating slightly until a solution
  2. customwas obtained
  3. temperatureto cool to room temperature
  4. filtrationPrecipitate was collected by filtration
  5. washwashed with ethyl acetate
  6. customdried in vacuo under a under high vacuum

Sources & evidence

ORD record
ord-26df85746d1c4940ac70b7322a1af6b6
Source dataset
uspto-grants-2005_03
Patent number
US06870065B2

Reaction notes

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