Pyridine → N-(11-Carbomethoxyundecanoyl)-2-hydroxyaniline

HRID 1290717Notes

Reaction equation

HRID 1290717 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].N1C=CC=CC=1.[C:15]([O:30][CH3:31])(=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O-])=[O:27]>C(Cl)Cl>[C:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:27])([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 58012-AminophenolHCID 22672980Dodecanedioic acid, monomethyl ester

Product 1

HCID 18795789N-(11-Carbomethoxyundecanoyl)-2-hydroxyaniline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred near solution of 2-aminophenol (0.24 g, 2.2 mM) in anhydrous methylene chloride (25 mL) was added dry pyridine (0.66 mL) and the mixture cooled in an ice-water bath. A solution of (7) (0.525 g, 2.0 mM) in methylene chloride (2 mL) was added over 1 minute (2×1.5 mL methylene chloride rinses), and the mixture allowed to stir cold. After 30 minutes the bath was removed. After stirring overnight at ambient temperatures, the mixture was filtered, the solvents removed in vacuo, and the residue pumped to remove all traces of pyridine. The product, (44) was used as is in subsequent steps.

Workup

  1. temperaturethe mixture cooled in an ice-water bath
  2. customAfter 30 minutes the bath was removed
  3. stirringAfter stirring overnight at ambient temperatures
  4. filtrationthe mixture was filtered
  5. customthe solvents removed in vacuo
  6. customto remove all traces of pyridine

Sources & evidence

ORD record
ord-d0b992ae376147b9b6b103338a8fd4ff
Source dataset
uspto-grants-1998_05
Patent number
US05753641

Reaction notes

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