4-Hexyloxyaniline → HCID 22992865, compound

HRID 1168628Notes

Reaction equation

HRID 1168628 reaction equation
[CH2:1]([O:7][C:8]1[CH:14]=[CH:13][C:11]([NH2:12])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C[O:16][C:17](=O)[CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>CC1C=CC(C)=CC=1>[CH2:1]([O:7][C:8]1[CH:14]=[CH:13][C:11]([NH:12][C:17](=[O:16])[CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:10][CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 383604-HexyloxyanilineHCID 99597Methyl pivaloylacetate

Product 1

HCID 22992865HCID 22992865, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 7809P-XyleneSolvent

Procedure

4-Hexyloxyaniline (1, 1.00 g, 5.17 mmol) and methyl-4,4-dimethyl-3-oxopentanoate (1.65 mL, 10.3 mmol) were suspended in 5 mL p-xylene and heated to reflux for 17 hours. The reaction was cooled to room temperature and purified by flash chromatography on silica gel eluting with 10% acetone, hexane to yield a brown solid. Recrystallization from hexane provided 1.35 g (82%) of a white solid. mp 70-72° C.; Analysis calculated for C19H29NO3: C, 71.44; H, 9.15; N, 4.38. Found: C, 71.72; H, 9.42; N, 4.30.

Workup

  1. temperatureheated
  2. temperatureto reflux for 17 hours
  3. custompurified by flash chromatography on silica gel eluting with 10% acetone, hexane
  4. customto yield a brown solid
  5. customRecrystallization from hexane

Sources & evidence

ORD record
ord-59bcb328b7c345c4821a023935874822
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

Loading…